[ CAS No. 874-14-6 ] {[proInfo.proName]}

Name: 874-14-6|1,3-Dimethylpyrimidine-2,4(1H,3H)-dione|97%
Brand: Ambeed
SKU: A184839
Price: 13.0 USD
Availability: InStock
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3d Animation Molecule Structure of 874-14-6

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Quality Control of [ 874-14-6 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 874-14-6 ]

Product Details of [ 874-14-6 ]

CAS No. :	874-14-6	MDL No. :	MFCD00038065
Formula :	C₆H₈N₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	JSDBKAHWADVXFU-UHFFFAOYSA-N
M.W :	140.14	Pubchem ID :	70122
Synonyms :

Calculated chemistry of [ 874-14-6 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.33
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	37.49
TPSA :	44.0 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.54 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.54
Log Po/w (XLOGP3) :	-0.54
Log Po/w (WLOGP) :	-0.92
Log Po/w (MLOGP) :	-0.01
Log Po/w (SILICOS-IT) :	-0.03
Consensus Log Po/w :	0.01

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-0.81
Solubility :	21.6 mg/ml ; 0.154 mol/l
Class :	Very soluble
Log S (Ali) :	0.09
Solubility :	170.0 mg/ml ; 1.22 mol/l
Class :	Highly soluble
Log S (SILICOS-IT) :	-0.56
Solubility :	38.3 mg/ml ; 0.274 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.59

Safety of [ 874-14-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 874-14-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 874-14-6 ]
Downstream synthetic route of [ 874-14-6 ]

[ 874-14-6 ] Synthesis Path-Upstream 1~7

1
[ 874-14-6 ]
[ 17356-08-0 ]
[ 141-90-2 ]

Reference： [1] Heterocycles, 1984, vol. 21, # 1, p. 289 - 307

2
[ 71-30-7 ]
[ 616-38-6 ]
[ 1122-47-0 ]
[ 6220-49-1 ]
[ 874-14-6 ]
[ 2228-27-5 ]
[ 124210-93-1 ]
[ 124210-92-0 ]

Reference： [1] Zeitschrift fuer Naturforschung, B: Chemical Sciences, 1989, vol. 44, # 7, p. 863 - 865

3
[ 18002-25-0 ]
[ 77-78-1 ]
[ 615-77-0 ]
[ 3551-55-1 ]
[ 874-14-6 ]
[ 7152-66-1 ]

Reference： [1] Tetrahedron, 2006, vol. 62, # 29, p. 6848 - 6854

4
[ 874-14-6 ]
[ 107-91-5 ]
[ 35441-10-2 ]

Reference： [1] Journal of Organic Chemistry, 1981, vol. 46, # 5, p. 846 - 851
[2] Journal of Organic Chemistry, 1981, vol. 46, # 5, p. 846 - 851
[3] Chemical and Pharmaceutical Bulletin, 1993, vol. 41, # 9, p. 1498 - 1506

5
[ 874-14-6 ]
[ 1225387-53-0 ]
[ 29274-22-4 ]

Yield	Reaction Conditions	Operation in experiment
58%	With sodium ethanolate In ethanol at 60℃; for 2 h;	1,3-Dimethyl uracil (3.15 g, 22.5 mmol) and sodium ethoxide (23 mL of a 21percent solution in ethanol) were added to a solution of lH-pyrazol-5 -amine (1.7 g, 20.4 mmol) in ethanol (50 mL). The resulting mixture was heated to 60 ⁰C for 2 h and was then cooled to room temperature. The pale brown solid was isolated by filtration to give pyrazolo[l,5-a]pyrimidin- 5(4H)-one (1.6 g, 58percent). Retention time (min) = 0.820, method [3], MS(ESI) 136.1 (M+Η).
12.50 g	With sodium ethanolate In ethanol at 80℃; for 5 h;	A mixture of A-5 (8.00 g, 96.28 mmol), 1,3-dimethylpyrimidine-2,4-dione (13.49 g, 96.28 mmol) and EtONa (32.76 g, 481.40 mmol) in EtOH (150 mL) was stirred at 80 °C for 5 hours. The solid was collected by filtration, washed with EtOH (50 mL), and dried in an oven to afford A-6 (12.50 g, 92.51 mmol) as a solid. 1H NMR (400MHz, DMSO-d6) δ 11 7.97 (d, 1H), 7.43 (d, 1H), 5.62 (d, 1H), 5.35 (d, 1H).

Reference： [1] Patent: WO2010/91310, 2010, A1, . Location in patent: Page/Page column 141
[2] Journal of Organic Chemistry, 2007, vol. 72, # 3, p. 1043 - 1046
[3] Patent: WO2018/98500, 2018, A1, . Location in patent: Page/Page column 84

6
[ 874-14-6 ]
[ 1820-80-0 ]
[ 29274-22-4 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 18, p. 5521 - 5527

7
[ 874-14-6 ]
[ 68-12-2 ]
[ 4869-46-9 ]

Reference： [1] Archiv der Pharmazie, 1991, vol. 324, # 4, p. 203 - 207
[2] Journal of Organic Chemistry, 1985, vol. 50, # 9, p. 1512 - 1516
[3] Tetrahedron, 2003, vol. 59, # 3, p. 341 - 352
[4] Journal of Heterocyclic Chemistry, 2009, vol. 46, # 6, p. 1280 - 1284
[5] Arkivoc, 2016, vol. 2017, # 2, p. 149 - 161

[ 874-14-6 ] Synthesis Path-Downstream 1~88

1
[ 874-14-6 ]
[ 7033-39-8 ]

Yield	Reaction Conditions	Operation in experiment
71%	With [bis(acetoxy)iodo]benzene; hydrogen bromide; In 1,2-dichloro-ethane; at 50℃; for 1.5h;	General procedure: To an 8 mL dram vial was added iodobenzene diacetate (0.6 mmol, 1.5 equiv), arene (0.4 mmol,1 eq.), dichloroethane (2 mL), then 1 M hydrochloric acid (2 mL, 5 equiv). The solution wasallowed to stir (1000 rpm) at 50 C for the indicated amount of time. After which the solution waswashed with saturated sodium bicarbonate, followed by saturated sodium thiosulfate andconcentrated. The crude mixture was then purified by column chromatography.

Reference： [1]Journal of the Chemical Society. Perkin transactions II,1993,p. 1487 - 1490
[2]Tetrahedron Letters,1992,vol. 33,p. 7779 - 7782
[3]Acta Chemica Scandinavica,1993,vol. 47,p. 1117 - 1121
[4]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1990,vol. 29,p. 539 - 544
[5]Journal of Organic Chemistry,1990,vol. 55,p. 4928 - 4933
[6]Chemistry Letters,1986,p. 1319 - 1322
[7]Chem,2019,vol. 5,p. 417 - 428
[8]Bulletin of the Korean Chemical Society,2012,vol. 33,p. 1357 - 1359
[9]Journal of Organic Chemistry,1980,vol. 45,p. 830 - 835
[10]Journal of Organic Chemistry,1959,vol. 24,p. 11
[11]Synthetic Communications,1985,vol. 15,p. 1001 - 1006
[12]Recueil des Travaux Chimiques des Pays-Bas,1981,vol. 100,p. 267 - 271

2
[ 66-22-8 ]
[ 77-78-1 ]
[ 874-14-6 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1990,vol. 29,p. 539 - 544
[2]Archiv der Pharmazie,1991,vol. 324,p. 203 - 207
[3]Chemistry Letters,1981,p. 1143 - 1146
[4]Chemistry - A European Journal,1999,vol. 5,p. 3549 - 3561
[5]Organic Letters,2016,vol. 18,p. 3710 - 3713
[6]Journal of Physical Chemistry A,1997,vol. 101,p. 4332 - 4337
[7]Journal of the American Chemical Society,1926,vol. 48,p. 2382
[8]Synthesis,1985,vol. NO. 5,p. 543 - 545
[9]Helvetica Chimica Acta,1993,vol. 76,p. 1916 - 1927
[10]Journal of Organic Chemistry,1985,vol. 50,p. 1512 - 1516
[11]Bioorganic Chemistry,2003,vol. 31,p. 357 - 366
[12]Journal of Heterocyclic Chemistry,2009,vol. 46,p. 1280 - 1284
[13]Arkivoc,2016,vol. 2017,p. 149 - 161

3
[ 1122-12-9 ]
[ 874-14-6 ]
[ 52695-25-7 ]

Reference： [1]Chemische Berichte,1974,vol. 107,p. 1265 - 1270

4
[ 120-72-9 ]
[ 4869-46-9 ]
[ 874-14-6 ]

Reference： [1]Tetrahedron,1990,vol. 46,p. 2367 - 2370
[2]Tetrahedron,1990,vol. 46,p. 2367 - 2370

5
[ 75-91-2 ]
[ 874-14-6 ]
[ 7033-39-8 ]
trans-5-bromo-6-tert-butoxy-1,3-dimethyluracil [ No CAS ]

Reference： [1]Acta Chemica Scandinavica,1993,vol. 47,p. 1117 - 1121

6
[ 874-14-6 ]
[ 64-17-5 ]
(5R,6R)-6-Ethoxy-5-iodo-1,3-dimethyl-dihydro-pyrimidine-2,4-dione [ No CAS ]
[ 40738-83-8 ]

Reference： [1]Recueil des Travaux Chimiques des Pays-Bas,1981,vol. 100,p. 267 - 271

7
[ 874-14-6 ]
[ 64781-79-9 ]
[ 104556-85-6 ]

Reference： [1]Journal of Heterocyclic Chemistry,1986,vol. 23,p. 349 - 352

8
[ 874-14-6 ]
[ 68-12-2 ]
[ 4869-46-9 ]

Reference： [1]Archiv der Pharmazie,1991,vol. 324,p. 203 - 207
[2]Journal of Organic Chemistry,1985,vol. 50,p. 1512 - 1516
[3]Tetrahedron,2003,vol. 59,p. 341 - 352
[4]Journal of Heterocyclic Chemistry,2009,vol. 46,p. 1280 - 1284
[5]Arkivoc,2016,vol. 2017,p. 149 - 161

9
[ 874-14-6 ]
[ 937-14-4 ]
[ 7033-39-8 ]
[ 92207-40-4 ]
trans-5-bromo-1,3-dimethyl-6-hydroxyuracil [ No CAS ]
cis-5-bromo-1,3-dimethyl-6-hydroxyuracil [ No CAS ]

Reference： [1]Acta Chemica Scandinavica,1993,vol. 47,p. 1117 - 1121
[2]Acta Chemica Scandinavica,1993,vol. 47,p. 1117 - 1121

10
[ 874-14-6 ]
[ 107-91-5 ]
[ 35441-10-2 ]

Reference： [1]Journal of Organic Chemistry,1981,vol. 46,p. 846 - 851
[2]Journal of Organic Chemistry,1981,vol. 46,p. 846 - 851
[3]Chemical and Pharmaceutical Bulletin,1993,vol. 41,p. 1498 - 1506

11
[ 874-14-6 ]
[ 31217-00-2 ]

Yield	Reaction Conditions	Operation in experiment
86%	With hydrogenchloride; [bis(acetoxy)iodo]benzene; In water; 1,2-dichloro-ethane; at 50℃; for 0.666667h;	General procedure: To an 8 mL dram vial was added iodobenzene diacetate (0.6 mmol, 1.5 equiv), arene (0.4 mmol,1 eq.), dichloroethane (2 mL), then 1 M hydrochloric acid (2 mL, 5 equiv). The solution wasallowed to stir (1000 rpm) at 50 C for the indicated amount of time. After which the solution waswashed with saturated sodium bicarbonate, followed by saturated sodium thiosulfate andconcentrated. The crude mixture was then purified by column chromatography.
65%	With ammonium cerium (IV) nitrate; lithium chloride; In acetic acid; acetonitrile; at 80℃; for 5.5h;Inert atmosphere;	Intermediate 8: 2,5,6-Trichloronicotinamide[0532] Into a 5000-mL 4-necked round-bottom flask, purged and maintained with an inert atmosphere of nitrogen, were placed l,3-dimethylpyrimidine-2,4(lH,3H)- dione (200 g, 1.43mol, 1.00 equiv), LiCl (72 g, 1.71mol, 1.20 equiv), CAN (1566 g, 2.86 mol, 2.00 equiv), acetonitrile (1500mL) and acetic acid (1500 mL). The resulting solution was stirred for 5.5 h at 80 C. The resulting mixture was cooled and concentrated under vacuum. The residue was diluted with 1500 mL of H20, then extracted with 3x500 mL of dichloromethane. The organic layers were combined, washed with 200 mL of water, dried and concentrated under vacuum. This resulted in 180 g (65%) of 5-chloro-l,3-dimethylpyrimidine-2,4(lH,3H)-dione as a white solid.

Reference： [1]Heterocycles,2005,vol. 66,p. 51 - 56
[2]Chem,2019,vol. 5,p. 417 - 428
[3]Tetrahedron Letters,1992,vol. 33,p. 7779 - 7782
[4]Bulletin of the Korean Chemical Society,2012,vol. 33,p. 1357 - 1359
[5]Journal of Organic Chemistry,1990,vol. 55,p. 4928 - 4933
[6]Patent: WO2011/94450,2011,A1 .Location in patent: Page/Page column 156-157

12
[ 874-14-6 ]
[ 40738-83-8 ]

Reference： [1]Journal of Organic Chemistry,1990,vol. 55,p. 4928 - 4933
[2]Tetrahedron Letters,1992,vol. 33,p. 7779 - 7782
[3]Chemical Communications,1997,p. 1355 - 1356
[4]Chemical Communications,2015,vol. 51,p. 17744 - 17747
[5]Journal of Heterocyclic Chemistry,1991,vol. 28,p. 509 - 512
[6]Synthetic Communications,1988,vol. 18,p. 855 - 868
[7]Chemistry Letters,1986,p. 1319 - 1322
[8]Recueil des Travaux Chimiques des Pays-Bas,1981,vol. 100,p. 267 - 271

13
[ 109-80-8 ]
[ 7033-39-8 ]
[ 874-14-6 ]
<6-(3-mercaptopropylthio)-1,3-dimethyluracil>disulfide [ No CAS ]

Reference： [1]Journal of Chemical Research, Miniprint,1992,p. 343 - 359

14
[ 91-16-7 ]
[ 7033-39-8 ]
[ 874-14-6 ]
[ 94937-46-9 ]
[ 105202-47-9 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1988,vol. 36,p. 4737 - 4748

15
[ 7033-39-8 ]
[ 107-03-9 ]
[ 874-14-6 ]
[ 120289-79-4 ]
[ 120289-82-9 ]

Reference： [1]Journal of Chemical Research, Miniprint,1992,p. 343 - 359
[2]Journal of Chemical Research, Miniprint,1992,p. 343 - 359
[3]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1989,vol. 28,p. 1079 - 1081
[4]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1989,vol. 28,p. 1079 - 1081
[5]Journal of Chemical Research, Miniprint,1992,p. 343 - 359
[6]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1989,vol. 28,p. 1079 - 1081

16
[ 7033-39-8 ]
[ 870-23-5 ]
[ 874-14-6 ]
[ 120289-80-7 ]

Reference： [1]Journal of Chemical Research, Miniprint,1992,p. 343 - 359

17
[ 7033-39-8 ]
[ 5548-09-4 ]
[ 874-14-6 ]
[ 66723-76-0 ]

Reference： [1]Journal of the American Chemical Society,1980,vol. 102,p. 7535

18
[ 7033-39-8 ]
[ 127-19-5 ]
[ 874-14-6 ]
[ 10320-84-0 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1981,p. 3114 - 3117

19
[ 7033-39-8 ]
[ 5466-06-8 ]
[ 874-14-6 ]
[ 139455-61-1 ]

Reference： [1]Journal of Chemical Research, Miniprint,1992,p. 343 - 359

20
[ 7033-39-8 ]
[ 106-42-3 ]
[ 874-14-6 ]
[ 110225-42-8 ]
[ 110225-41-7 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1988,vol. 36,p. 4737 - 4748
[2]Chemical and Pharmaceutical Bulletin,1988,vol. 36,p. 4737 - 4748

21
[ 7033-39-8 ]
[ 75-24-1 ]
[ 874-14-6 ]
[ 4401-71-2 ]

Reference： [1]Synthesis,1993,p. 213 - 215

22
[ 7033-39-8 ]
[ 108-98-5 ]
[ 874-14-6 ]
[ 55832-80-9 ]

Reference： [1]Journal of Chemical Research, Miniprint,1992,p. 343 - 359

23
[ 7033-39-8 ]
[ 623-51-8 ]
[ 874-14-6 ]
[ 128499-39-8 ]
[ 36235-61-7 ]

Reference： [1]Journal of Chemical Research, Miniprint,1992,p. 343 - 359

24
[ 7033-39-8 ]
[ 100-53-8 ]
[ 874-14-6 ]
[ 120289-78-3 ]
[ 120289-81-8 ]

Reference： [1]Journal of Chemical Research, Miniprint,1992,p. 343 - 359
[2]Journal of Chemical Research, Miniprint,1992,p. 343 - 359

25
[ 7033-39-8 ]
[ 874-14-6 ]

Reference： [1]Journal of Organic Chemistry,2001,vol. 66,p. 3610 - 3612
[2]Tetrahedron,1983,vol. 39,p. 3919 - 3922
[3]Journal of the American Chemical Society,1980,vol. 102,p. 7535

26
[ 7033-39-8 ]
[ 874-14-6 ]
[ 10320-84-0 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1981,p. 3114 - 3117

27
[ 7033-39-8 ]
[ 874-14-6 ]
[ 110225-42-8 ]
[ 110225-41-7 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1988,vol. 36,p. 4737 - 4748

28
[ 874-14-6 ]
[ 1820-80-0 ]
[ 29274-23-5 ]

Yield	Reaction Conditions	Operation in experiment
72%		A mixture of <strong>[874-14-6]1,3-dimethyluracil</strong> (4.7 g, 1.4 eq.) and 3-aminopyrazole (2.0 g, 24.1 mmol) was heated to reflux in 1M NaOEt in EtOH (31 mL) for one hour. The resulting solution was cooled to 0° C. The resulting precipitate was dissolved in water and neutralized with acetic acid and cooled to 0° C. The precipitate was collected and dried under reduced pressure to yield a cream-colored solid (2.4 g, 72percent yield): M+H=136.

Reference： [1]Patent: US2007/82901,2007,A1 .Location in patent: Page/Page column 21
[2]Journal of Heterocyclic Chemistry,1986,vol. 23,p. 349 - 352

29
[ 4869-46-9 ]
[ 874-14-6 ]
pyrazole-4-carbohydrazide [ No CAS ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1983,p. 1293 - 1298

30
[ 129-00-0 ]
[ 40738-83-8 ]
[ 874-14-6 ]
1,3-dimethyl-5-(pyren-1-yl)pyrimidine-2,4(1H,3H)-dione [ No CAS ]

Reference： [1]Tetrahedron Letters,1980,vol. 21,p. 2813 - 2816
[2]Tetrahedron Letters,1980,vol. 21,p. 2813 - 2816

31
[ 18293-99-7 ]
[ 40738-83-8 ]
[ 874-14-6 ]
[ 99044-63-0 ]
[ 99044-64-1 ]

Reference： [1]Tetrahedron Letters,1985,vol. 26,p. 1993 - 1994
[2]Journal of Organic Chemistry,1986,vol. 51,p. 5148 - 5153

32
[ 85-01-8 ]
[ 40738-83-8 ]
[ 874-14-6 ]
[ 75759-67-0 ]

Reference： [1]Tetrahedron Letters,1980,vol. 21,p. 2813 - 2816

33
[ 75-24-1 ]
[ 40738-83-8 ]
[ 874-14-6 ]
[ 4401-71-2 ]

Reference： [1]Synthesis,1993,p. 213 - 215

34
[ 40738-83-8 ]
[ 762-72-1 ]
[ 874-14-6 ]
[ 105183-69-5 ]

Reference： [1]Journal of Organic Chemistry,1986,vol. 51,p. 5148 - 5153

35
[ 874-14-6 ]
[ 5176-82-9 ]
[ 7033-39-8 ]
[ 27994-76-9 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1989,vol. 62,p. 3750 - 3751

36
[ 7033-39-8 ]
[ 13133-62-5 ]
[ 874-14-6 ]
[ 55832-80-9 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1989,vol. 28,p. 1079 - 1081

37
[ 7033-39-8 ]
[ 32894-07-8 ]
[ 874-14-6 ]
[ 120289-78-3 ]
[ 120289-81-8 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1989,vol. 28,p. 1079 - 1081
[2]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1989,vol. 28,p. 1079 - 1081

38
[ 7033-39-8 ]
[ 87234-43-3 ]
[ 874-14-6 ]
[ 120289-80-7 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1989,vol. 28,p. 1079 - 1081

39
[ 7033-39-8 ]
[ 128499-42-3 ]
[ 874-14-6 ]
[ 128499-39-8 ]
[ 36235-61-7 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1989,vol. 28,p. 1079 - 1081

40
[ 7033-39-8 ]
[ 60-24-2 ]
[ 874-14-6 ]
[ 128499-40-1 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1989,vol. 28,p. 1079 - 1081

41
[ 874-14-6 ]
[ 2923-16-2 ]
[ 85199-76-4 ]
[ 85199-75-3 ]

Reference： [1]Zeitschrift fur Naturforschung, B: Chemical Sciences,1997,vol. 52,p. 742 - 748

42
[ 874-14-6 ]
[ 1666-13-3 ]
[ 135067-69-5 ]

Yield	Reaction Conditions	Operation in experiment
93%	With dihydrogen peroxide; sodium iodide; In dimethyl sulfoxide; at 50℃; for 3h;Schlenk technique;	0.2 mmol of <strong>[874-14-6]1,3-dimethyluracil</strong>, 0.1 mmol of NaI and 0.3 mmol of diphenyl diselenide and a stir bar were added to a clean Schlenk reaction tube.Then add 3 mL of DMSO solvent with a syringe.Finally, 0.6 mmol H2O2 was added with a micro-syringe, and reacted at 50 C for 3 hours, and detected by TLC dot plate; after the reaction was completed,The reaction solution was added with water and extracted with ethyl acetate three times.The organic layer is concentrated and separated by column chromatography to obtain pure5-phenylseleno-(1,3-dimethyl)-uracil, white solid, yield 93%.
70%	With dipotassium peroxodisulfate; iodine; In acetonitrile; at 60℃;	General procedure: An 8 mL oven-dried scintillation vial equipped with a magnetic stir bar was charged with a mixture of 4-quinolone or uracil (0.50 mmol, 1.0 equiv), disulfide or thiol (0.75 mmol, 1.5 equiv), molecular iodine (I2) (128 mg, 0.50 mmol, 1.0 equiv), K2S2O8 (1.00-1.50 mmol, 2.0-3.0 equiv), and acetonitrile (CH3CN) (1 mL). The vial was capped, and the reaction mixture was stirred at 60 or 80 C for 12-16 h. Upon completion, saturated Na2S2O3 (5 mL) and distilled deionized H2O (10 mL) was added, and the mixture was extracted with ethyl acetate (3 x 25 mL). The combined organic layer was washed with saturated NaCl, dried over anhydrous Na2SO4, and concentrated in vacuo. The crude product was purified by SiO2 column chromatography to afford the desired thioether products.

Reference： [1]Heterocycles,1998,vol. 48,p. 437 - 441
[2]Patent: CN109651267,2019,A .Location in patent: Paragraph 0225-0230
[3]Organic Letters,2019,vol. 21,p. 6643 - 6647
[4]Journal of Organic Chemistry,1999,vol. 64,p. 7290 - 7298
[5]Tetrahedron,2019,vol. 75
[6]European Journal of Organic Chemistry,2019,vol. 2019,p. 2759 - 2766

43
[ 874-14-6 ]
[ 7726-95-6 ]
[ 7033-39-8 ]

Reference： [1]Journal of Organic Chemistry,1959,vol. 24,p. 11

44
[ 874-14-6 ]
[ 32446-66-5 ]
(Z)-8,8-bis(4-cyanophenyl)-2,4-dimethyl-7-oxa-2,4-diazabicyclo[4.2.0]octane-3,5-dione [ No CAS ]
(Z)-7,7-bis(4-cyanophenyl)-2,4-dimethyl-8-oxa-2,4-diazabicyclo[4.2.0]octane-3,5-dione [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2006,p. 1790 - 1800
[2]Beilstein Journal of Organic Chemistry,2011,vol. 7,p. 113 - 118

45
[ 874-14-6 ]
[ 882-33-7 ]
[ 55832-80-9 ]

Yield	Reaction Conditions	Operation in experiment
82%	With dipotassium peroxodisulfate; iodine; In acetonitrile; at 60℃;	General procedure: An 8 mL oven-dried scintillation vial equipped with a magnetic stir bar was charged with a mixture of 4-quinolone or uracil (0.50 mmol, 1.0 equiv), disulfide or thiol (0.75 mmol, 1.5 equiv), molecular iodine (I2) (128 mg, 0.50 mmol, 1.0 equiv), K2S2O8 (1.00-1.50 mmol, 2.0-3.0 equiv), and acetonitrile (CH3CN) (1 mL). The vial was capped, and the reaction mixture was stirred at 60 or 80 C for 12-16 h. Upon completion, saturated Na2S2O3 (5 mL) and distilled deionized H2O (10 mL) was added, and the mixture was extracted with ethyl acetate (3 x 25 mL). The combined organic layer was washed with saturated NaCl, dried over anhydrous Na2SO4, and concentrated in vacuo. The crude product was purified by SiO2 column chromatography to afford the desired thioether products.

Reference： [1]Tetrahedron,2019,vol. 75
[2]Heterocycles,1998,vol. 48,p. 437 - 441
[3]European Journal of Organic Chemistry,2019,vol. 2019,p. 2759 - 2766

46
[ 874-14-6 ]
[ 1260243-04-6 ]
ethyl 5-oxo-4,5-dihydropyrazolo[1,5-a]pyrimidine-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	With sodium ethanolate; In ethanol; at 90℃; for 3h;Inert atmosphere;	To a solution of sodium ethoxide (520mg, 7.6mmol) in EtOH (20mL) were added ethyl 3- amino-lH-pyrazole-4-carboxylate (1 g, 6.45 mmol) and solid <strong>[874-14-6]1,3-dimethyluracil</strong> (1.35g, 9.68mmol), under a N2atmosphere. The reaction mixture was stirred at 90 C for 3 h then cooled to 0 C in ice-water bath. Amber precipitate was appeared. The resulting amber precipitate was filtered off and dissolved in water (25 mL) and then the resulting solution was neutralized with acetic acid. White solid was appeared, filtered and collected the solid, and then azeotroped to dryness by refluxing in toluene (100 mL) to give the title compound as a white solid (900 mg, 67%). H NMR (300 MHz, DMSO-Lambda): delta (ppm) 11.78 (brs, 1H), 8.58 (d, J = 8.0 Hz, 1H), 8.15 (s, 1H), 6.16 (d, J= 7.9 Hz, 1H), 4.28 (q, J= 7.0 Hz, 2H), 1.29 (t, J= 7.0 Hz, 3H).
67%	With sodium ethanolate; In ethanol; at 90℃; for 3h;	To a solution of sodium ethoxide (520 mg, 7.6 mmol)In EtOH (20 mL)A solution of ethyl 3-amino-1H-pyrazole-4-carboxylate (1 g, 6.45 mmol) and <strong>[874-14-6]1,3-dimethyluracil</strong> (1.35 g, 9.68 mmol) were added sequentially.After the reaction system was stirred at 90 C for 3 hours,Move to an ice-water bath to cool and precipitate with amber. The filter cake was collected by filtration and washed with water (25 mL). The resulting solution was adjusted to pH = 7 with acetic acid and precipitated as a white solid which was filtered. Toluene (100 mL) was added to the resulting solid and dried in an ether to give the title compound as an off-white solid (900 mg, 67%).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 3149 - 3153
[2]Patent: WO2015/73267,2015,A1 .Location in patent: Paragraph 384
[3]Patent: CN104650092,2017,B .Location in patent: Paragraph 0745-0746; 0754-0755
[4]Journal of Organic Chemistry,2007,vol. 72,p. 1043 - 1046

47
[ 874-14-6 ]
[ 1225387-53-0 ]
[ 29274-22-4 ]

Yield	Reaction Conditions	Operation in experiment
58%	With sodium ethanolate; In ethanol; at 60℃; for 2h;	1,3-Dimethyl uracil (3.15 g, 22.5 mmol) and sodium ethoxide (23 mL of a 21% solution in ethanol) were added to a solution of lH-pyrazol-5 -amine (1.7 g, 20.4 mmol) in ethanol (50 mL). The resulting mixture was heated to 60 0C for 2 h and was then cooled to room temperature. The pale brown solid was isolated by filtration to give pyrazolo[l,5-a]pyrimidin- 5(4H)-one (1.6 g, 58%). Retention time (min) = 0.820, method [3], MS(ESI) 136.1 (M+Eta).
12.50 g	With sodium ethanolate; In ethanol; at 80℃; for 5h;	A mixture of A-5 (8.00 g, 96.28 mmol), 1,3-dimethylpyrimidine-2,4-dione (13.49 g, 96.28 mmol) and EtONa (32.76 g, 481.40 mmol) in EtOH (150 mL) was stirred at 80 C for 5 hours. The solid was collected by filtration, washed with EtOH (50 mL), and dried in an oven to afford A-6 (12.50 g, 92.51 mmol) as a solid. 1H NMR (400MHz, DMSO-d6) delta 11 7.97 (d, 1H), 7.43 (d, 1H), 5.62 (d, 1H), 5.35 (d, 1H).

Reference： [1]Patent: WO2010/91310,2010,A1 .Location in patent: Page/Page column 141
[2]Journal of Organic Chemistry,2007,vol. 72,p. 1043 - 1046
[3]Patent: WO2018/98500,2018,A1 .Location in patent: Page/Page column 84

48
[ 874-14-6 ]
[ 2314-97-8 ]
[ 85199-75-3 ]

Yield	Reaction Conditions	Operation in experiment
53%	With caesium carbonate; In dimethyl sulfoxide; for 24h;Inert atmosphere; Irradiation;	In a 25 mL reaction tube,Add Cs2CO3 (0.8 mmol),Compound A-2 (0.4 mmol, 1 equivalent),After replacing the argon three times, add 3 mL of dimethyl sulfoxide (DMSO).100 muL (1.20 mmol) of Compound B in DMSO was injected.After stirring for 24 hours under blue light,Compound C-2,The yield was 53percent.
44%	With iron(III) sulfate; sulfuric acid; dihydrogen peroxide; In water; dimethyl sulfoxide; at 40 - 50℃; for 0.333333h;	0.14 g (1.0 mmol) of <strong>[874-14-6]1,3-dimethyluracil</strong> was weighed and placed in a 50 ml two-neck flask equipped with a magnetic rotor and the atmosphere in the flask was replaced with argon. The following materials were added thereinto: 2.0 ml of a 1N dimethyl sulfoxide solution of sulfuric acid, 1.0 ml of a 3.0 mol/l dimethyl sulfoxide solution of trifluoromethyl iodide, 0.2 ml of a 30percent hydrogen peroxide aqueous solution and 0.3 ml of a 1.0 mol/l aqueous solution of ferric sulfate. The mixture was stirred at 40 to 50°C for 20 minutes and then the resulting solution was cooled to room temperature. Formation of 1,3-dimethyl-5-trifluoromethyluracil (19F-NMR yield: 78percent) was confirmed by 19F-NMR with 2,2,2-trifluoroethanol as an internal standard. 1,3-Dimethyl-5-trifluoromethyluracil was obtained as a white solid (0.12 g, yield: 44percent) by preparative thin-layer chromatography. 1H-NMR (deuterated acetone): delta3.25(s, 3H), 3.51(s, 3H), 8.23(q, JHF=1.05Hz, 1H). 13C-NMR (deuterated acetone): delta27.8, 37.6, 102.9(q, JCF=32.3Hz), 123. 8 (q, JCF=268.4Hz), 146.4 (q, JCF=5. 91Hz), 151.9, 159.5. 19F-NMR (deuterated acetone): delta-60.6. MS (m/z): 208[M]+.

Reference： [1]Patent: CN108484508,2018,A .Location in patent: Paragraph 0048; 0049; 0050
[2]Chemical Communications,2018,vol. 54,p. 13662 - 13665
[3]Patent: EP1947092,2008,A1 .Location in patent: Page/Page column 39-40

49
[ 874-14-6 ]
[ 2740-81-0 ]
[ 107-14-2 ]
[ 75-05-8 ]
[ 639481-35-9 ]

Yield	Reaction Conditions	Operation in experiment
100%		[ACETONITRILE (10ML)] was added to a solution of sodium bis (trimethylsilyl) amide [(100ML,] 1. [OM IN THF, 100MMOL)] in THF (50mL) at-78 [°C] to give a thick white precipitate. 2-Chlorophenyl isothiocyanate (7.72g, 45. [45MMOL)] was added to give a brown solution. The mixture was allowed to warm to r. t. over 1 h then diluted with EtOH (50mL). N, N-Dimethyluracil (6.4g, [45MMOL)] was added and the mixture heated at reflux for 24h. Volatiles were removed in vacuo and the residue dissolved in acetonitrile [(100ML). CHLOROACETONITRILE] (2.85mL, [45MMOL)] was added and the mixture heated at 50 [°C] for 1 h, a second charge of chloroacetonitrile (2.85mL, [45MMOL)] was added and heating continued for 1.5h. Some of the acetonitrile [(-50ML)] was removed in vacuo and water was added to precipitate the product. The brown solid was filtered off, washed with water (50mL) and Et20 (50mL) and dried to give the title compound as a brown solid [(14.] 3g, quant.). [5H] (DMSO-d6) 8.10 (1 H, d, J 9.7Hz), 7.75-7. 73 (1H, m), 7.65-7. 54 (3H, m), 7.14 (2H, [BR S, NH2),] 6.54 [(1H,] d, J 9. 7Hz). LCMS [(ES+)] RT 2.97 minutes, 302 (M+H) [+.]
100%		Acetonitrile (10 ml) was added to a solution of sodium bis (trimethylsilyl) amide (100 ml, 1. OM in THF, 100 mmol) in THF (50 ml) at-78°C to give a thick white precipitate. 2-Chlorophenyl isothiocyanate (7.72 g, 45.45 mmol) was added to give a brown solution. The mixture was allowed to warm to r. t. over 1 h then diluted with EtOH (50ml). 1,3-Dimethyluracil (6.4 g, 45 mmol) was added and the mixture heated at reflux for 24 h. Volatiles were removed in vacuo and the residue dissolved in acetonitrile (100 ml). Chloroacetonitrile (2.85 ml, 45 mmol) was added and the mixture heated at 50°C for 1 h, a second charge of chloroacetonitrile (2.85 ml, 45 rmnol) was added and heating continued for 1.5 h. Some of the acetonitrile (-50 ml) was removed in vacuo and water was added to precipitate the product. The brown solid was filtered off, washed with water (50 ml) and EtzO (50 ml) and dried to give the title compound as a brown solid (14.3 g, quantitative). 8H (DMSO-d6) 8.10 (1H, d, J9.7 Hz), 7.75-7. 73 (1H, m), 7.65-7. 54 (3H, m), 7.14 (2H, br s, NH2), 6.54 (1H, d, J9. 7 Hz). LCMS (ES+) RT 2.97 minutes, 302 (M+H)+.
100%		Acetonitrile (10mL) was added to a solution of sodium bis (trimethylsilyl) amide (100ML, 1. OM in THF, 100MOL) in THF (50mL) AT-78°C to give a thick white precipitate. 2-Chlorophenyl isothiocyanate (7.72g, 45. 45MMOL) was added to give a brown solution. The mixture was allowed to warm to r. t. over 1 h then diluted with EtOH (50mL). N, N-Dimethyluracil (6.4g, 45mmol) was added and the mixture heated at reflux for 24 h. Volatiles were removed in vacuo and the residue dissolved in acetonitrile (100ML). Chloroacetonitrile (2.85mL, 45MMOL) was added and the mixture heated at 50°C for 1 h, a second charge of chloroacetonitrile (2.85mL, 45mmol) was added and heating continued for 1.5 h. Some of the acetonitrile (-50ML) was removed in vacuo and water was added to precipitate the product. The brown solid was filtered off, washed with water (50mL) and ETZO (50mL) and dried to give the title compound as a brown solid (14.3g, quant. ). 8H (DMSO-d6) 8. 10 (1H, d, J 9.7Hz), 7.75-7. 73 (1 H, m), 7.65-7. 54 (3H, m), 7.14 (2H, br s, NH2), 6.54 (1 H, d, J 9. 7HZ). LCMS (ES+) RT 2.97 minutes, 302 (M+H) +.

Reference： [1]Patent: WO2004/846,2003,A1 .Location in patent: Page 66
[2]Patent: WO2005/42540,2005,A1 .Location in patent: Page/Page column 44-45
[3]Patent: WO2004/113347,2004,A1 .Location in patent: Page 74

50
[ 874-14-6 ]
[ 580-13-2 ]
[ 1182815-70-8 ]
[ 1182815-60-6 ]

Yield	Reaction Conditions	Operation in experiment
8%; 68%	With palladium diacetate; potassium carbonate; triphenylphosphine; Trimethylacetic acid; In N,N-dimethyl-formamide; at 130℃; for 12h;Inert atmosphere;	General procedure: A stirred mixture of <strong>[874-14-6]1,3-dimethyluracil</strong> (1a, 140 mg, 1.0 mmol), bromobenzene (2a, 315 mg, 2.0 equiv), Pd(OAc)2 (22 mg, 10 mol percent), PPh3 (52 mg, 20 mol percent), PivOH (30 mg, 30 mol percent), K2CO3 (415 mg, 3.0 equiv) in DMF (1.5 mL) was heated to 130 °C for 12 h under nitrogen atmosphere. After the usual aqueous extractive workup with chloroform and column chromatographic purification process (hexanes/THF, 4:1) compounds 3a (171 mg, 79percent) and 4a (21 mg, 10percent) were obtained as white solids.5

Reference： [1]European Journal of Organic Chemistry,2009,p. 3698 - 3701
[2]Tetrahedron Letters,2011,vol. 52,p. 6228 - 6233
[3]European Journal of Organic Chemistry,2009,p. 3698 - 3701

51
[ 874-14-6 ]
[ 207974-17-2 ]
[ 75-05-8 ]
[ 851749-68-3 ]

Yield	Reaction Conditions	Operation in experiment
86%		A solution of sodium bis (trimethylsilyl) amide (351 ml of a 1M solution in THF, 351 mmol) in THF (150 ml) was cooled to-78°C and acetonitrile (30 ml) was added. After 20 min, 2,6-difluorophenyl isothiocyanate (30.0 g, 175.5 mmol) was added slowly over 5 min. The reaction mixture was allowed to warm slowly to r. t. over 2 h. EtOH (100 ml) was added followed by <strong>[874-14-6]1,3-dimethyluracil</strong> (27.0 g, 193.5 mmol) and the mixture heated to reflux for 18 h. After cooling, the mixture was concentrated in vacuo to a volume of approx. 150 ml and EtOH (75 ml) was added. This mixture was cooled and Et2O (approx. 750 ml) was added slowly to give a pale yellow precipitate. The solid was filtered off, washed with Et2O (2 x 100 ml) then dried to give the title compound as a yellow/pale brown solid (49.0 g, 86percent). 6H (DMSO-d6) 7.43-7. 33 (1H, m), 7.23 (1H, d, J 9.2 Hz), 7.13-7. 06 (2H, m), 5.64 (1H, d, J9. 2 Hz). LCMS (ES+) RT 7.0 minutes, 265 (M+H) +.

Reference： [1]Patent: WO2005/42540,2005,A1 .Location in patent: Page/Page column 85-86

52
[ 874-14-6 ]
[ 1820-80-0 ]
[ 1224944-43-7 ]

Yield	Reaction Conditions	Operation in experiment
95%	With sodium ethanolate; In ethanol; for 1h;Reflux; Inert atmosphere;	A mechanically stirred mixture of 3-aminopyrazole (9.38 g, 0.11 mM, 1.0 equiv), <strong>[874-14-6]1,3-dimethyluracil</strong> (14.7 g, 0.11 mM, 1.0 equiv) and 21percent sodium ethoxide in ethanol (170 mL, 5.0 equiv) was heated to reflux. Within minutes, a heavy precipitate formed. After refluxing for 1 hour, <strong>[874-14-6]1,3-dimethyluracil</strong> could no longer be detected by thin layer chromatography (tic) (92:8 dichloromethane (dichloromethane):MeOH). The reaction mixture was cooled, filtered, washed with cold ethanol and vacuum dried to give 13.47 g (95percent) of sodium pyrazolo[l,5-alpha]pyrimidin-5-olate. LCMS (ESI) m+H = 136.0; 1H NMR (400 MHz, OMSO-d6) delta: 8.0 (d, 1 H), 7.43 (d, 1 H), 5.65 (d, IH), 5.37 (d, 1 H).
95%	With sodium ethanolate; In ethanol; for 1h;Reflux; Inert atmosphere;	A mechanically stirred mixture of 3-aminopyrazole (9.38 g, 0.11 mM, 1.0 equiv), <strong>[874-14-6]1,3-dimethyluracil</strong> (14.7 g, 0.11 mM, 1.0 equiv) and 21percent sodium ethoxide in ethanol (170 mL, 5.0 equiv) was heated to reflux. Within minutes, a heavy precipitate formed. After refluxing for 1 hour, <strong>[874-14-6]1,3-dimethyluracil</strong> could no longer be detected by thin layer chromatography (tlc) (92:8 dichloromethane (dichloromethane):MeOH). The reaction mixture was cooled, filtered, washed with cold ethanol and vacuum dried to give 13.47 g (95percent) of sodium pyrazolo[1,5-a]pyrimidin-5-olate. LCMS (ESI) m+H=136.0; 1H NMR (400 MHz, DMSO-d6) delta: 8.0 (d, 1H), 7.43 (d, 1H), 5.65 (d, 1H), 5.37 (d, 1H).

Reference： [1]Patent: WO2010/51549,2010,A1 .Location in patent: Page/Page column 42; 74-75
[2]Patent: US2012/22043,2012,A1 .Location in patent: Page/Page column 32-33
[3]Journal of Medicinal Chemistry,2012,vol. 55,p. 10090 - 10107

53
[ 874-14-6 ]
[ 1820-80-0 ]
[ 29274-22-4 ]

Yield	Reaction Conditions	Operation in experiment
> 99%	With sodium; In ethanol;Reflux;	A solution of sodium metal (11.1 g, 481 mmol) in EtOH (344 mL) was added 1H-pyrazol-3-amine (20.0 g, 241 mmol) and <strong>[874-14-6]1,3-dimethylpyrimidine-2,4(1H,3H)-dione</strong> (35.4 g, 253 mmol) at room temperature. The reaction mixture was refluxed overnight and cooled to room temperature. A precipitated solid was collected by filtration, washed with cold EtOH and dried under vacuum to afford pyrazolo[1,5-a]pyrimidin-5-ol (36.0 g, >99percent) as a white solid. 1H-NMR (DMSO-d6, Varian, 400 MHz): delta 5.35 (1H, d, J=1.6 Hz), 5.63 (1H, d, J=7.2 Hz), 7.43 (1H, d, J=1.6 Hz), 7.97 (1H, d, J=7.2 Hz). * A proton from OH was not observed.
86%	With sodium methylate; In methanol; at 65 - 70℃; for 4h;Large scale;	Step 1, under anhydrous, oxygen-free and nitrogen-free protection, add 1.9kg to a mixture of 1kg of compound A and 2.7L of sodium methoxide in methanol (in which methanolic sodium methoxide solution, sodium methoxide mass fraction is 30percent) Compound B, heating, the temperature was controlled at 65-70 ° C, and the reaction was refluxed for 4 hours. After the reaction was completed, the reaction liquid was cooled and filtered, and the solvent was evaporated under reduced pressure to give a white solid, and then white solid was dissolved in 1.5 L at 10 ° C. In water, the pH was adjusted to 2, and 1.4 kg of white solid compound C was obtained by filtration, yield 86percent
53%		To a solution of dry EtOH (500 mL) was added sodium (22.1 g, 481 mmol) under a cold water bath. After complete dissolution, lH-pyrazol-3 -amine (40.0 g, 481 mmol) and l ,3-dimethylpyrimidine-2,4(lH,3H)-dione (101 g, 722 mmol) were added. The reaction mixture was heated at reflux for 4 hours. After cooling, the white solid was collected by filtration, washed with cold EtOH and dried under vacuum. The crude solid was suspended in minimum amount of water and the pH of the solution was adjusted to 5 by dropwise addition of acetic acid. The precipitated solid was collected by filtration, re- dissolved in MeOH and concentrated by rotary evaporation to azeotrope any remaining water to afford pyrazolo[l ,5-a]pyrimidin-5-ol (34.3 g, 53percent>).

Reference： [1]Patent: US2016/168156,2016,A1 .Location in patent: Paragraph 0350; 0352; 0353
[2]Patent: CN109251205,2019,A .Location in patent: Paragraph 0026; 0028
[3]Patent: WO2011/29027,2011,A1 .Location in patent: Page/Page column 42

54
[ 874-14-6 ]
[ 1820-80-0 ]
[ 29274-22-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 5521 - 5527

55
[ 874-14-6 ]
[ 1353628-07-5 ]
[ 1353628-56-4 ]

Yield	Reaction Conditions	Operation in experiment
80%	With sodium ethanolate; In ethanol; at 90℃; for 3h;	Intermediate 51Mixed intermediate 4 (1.33g, 5mmol) with dimethyl uracil (771mg, 5.5mmol) in anhydrous EtOH (12mL). Added 3M sodium ethoxide in ethanol (5.83mL, 17.5mmol). Stirred (at)90°C for 3hrs. Cooled to room temperature. Diluted with ethyl acetate and washed with saturated aqueous sodium bicarbonate solution twice and saturated aqueous sodium chloride solution. Dried organic extract over anhydrous sodium sulfate and then concentrated under reduced pressure. Purified with silica gel column (0-60percent EtOAc in hexanes) to give intermediate 51 (1.27g, 80percent yield). 1H NMR (400MHz, CD3OD): delta 8.29 (d, J=7.6Hz, 1H), 5.78 (d, J=8.0Hz, 1 H), 5.70 (s, 1 H), 5.40 (m, 1H), 4.01 (m, 1H), 2.89 (m, 1H), 2.34 (m, 1H), 1.80 (m, 1H), 1.63 (m, 2H), 1.54-1.45 (m, 1 1H).LC/MS m/z): 319.0 [M+H]+

Reference： [1]Patent: WO2011/163518,2011,A1 .Location in patent: Page/Page column 210-211

56
[ 874-14-6 ]
[ 41680-34-6 ]
[ 1224944-46-0 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium ethanolate; In ethanol; for 1h;Reflux; Inert atmosphere;	To a stirred solution of <strong>[41680-34-6]5-amino-1H-pyrazole-4-carboxylic acid</strong> (10.0 g, 71.4 mmol) in ethanol (100 mL), was added sodium ethoxide (17.0 g, 245 mmol) followed by 1,3-dimethyluracil (11.0 g, 78.6 mmol). The reaction mixture was then stirred at reflux overnight under an argon atmosphere. The mixture was poured into ice-water, and the resultant solution was acidified to about pH 3-4 with concentrated HCl. The suspension was stirred for 2 hours and then filtered to afford the intermediate, which was used without further purification (10.0 g, 58% yield). 1H NMR (400 MHz, DMSO-d6): 8.54 (d, J=9.2 Hz, 1H), 8.06 (s, 1H), 6.11 (d, J=7.2 Hz, 1H).

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 10090 - 10107
[2]Patent: US2012/22043,2012,A1 .Location in patent: Page/Page column 86

57
[ 874-14-6 ]
[ 55270-33-2 ]
[ 1493-13-6 ]
C₁₆H₁₃F₃IN₃O₅S [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 3772 - 3775

58
[ 1006-47-9 ]
[ 874-14-6 ]
[ 1493-13-6 ]
C₁₆H₁₃F₃IN₃O₅S [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 3772 - 3775

59
[ 874-14-6 ]
[ 23286-70-6 ]
[ 1431654-55-5 ]

Yield	Reaction Conditions	Operation in experiment
76%	With sodium ethanolate; In ethanol; at 140℃; for 2h;	Sodium ethoxide (4.02 g, 59.10 mmol) was added to a solution of ethyl 5-amino-3-methyl-1H-pyrazole-4-carboxylate (10.0 g, 59.10 mmol) and <strong>[874-14-6]1,3-dimethyluracil</strong> (8.28 g, 59.10 mmol) in EtOH (50 mL). The reaction mixture was stirred at 140 °C for 2 h. After cooling to room temp the solid was collected by filtration. The solid was dissolved in H2O (100 mL) and the pH was adjusted to 7. The resulting precipitate was collected by filtration and dried under vacuum to give ethyl 2-methyl-5-oxo-4,5-dihydropyrazolo[1,5-a]pyrimidine-3-carboxylate (10.0 g, 76percent yield). MS (ESI) calcd for C10H11N3O3 (m/z): 221.08
76%	With sodium ethanolate; In ethanol; at 140℃; for 2h;	Sodium ethoxide (4.02 g, 59.10 mmol) was added to a solution of ethyl 5-amino-3-methyl-1H-pyrazole-4-carboxylate (10.0 g, 59.10 mmol) and <strong>[874-14-6]1,3-dimethyluracil</strong> (8.28 g, 59.10 mmol) in EtOH (50 mL). The reaction mixture was stirred at 140 °C for 2 h. After cooling to room temp the solid was collected by filtration. The solid was dissolved in H2O (100 mL) and the pH was adjusted to 7. The resulting precipitate was collected by filtration and dried under vacuum to give ethyl 2-methyl-5-oxo-4,5-dihydropyrazolo[1,5-a]pyrimidine-3-carboxylate (10.0 g, 76percent yield). MS (ESI) calcd for C10H11N3O3 (m/z): 221.08

Reference： [1]Patent: WO2013/59587,2013,A1 .Location in patent: Page/Page column 144; 145
[2]Patent: EP2768509,2017,B1 .Location in patent: Paragraph 0516; 0517

60
[ 874-14-6 ]
[ 16419-60-6 ]
[ 105202-37-7 ]

Yield	Reaction Conditions	Operation in experiment
70%	With 1,10-Phenanthroline; oxygen; palladium diacetate; In N,N-dimethyl-formamide; at 90℃; for 16h;	General procedure: Uracil1 (1 mmol), the arylboronic acid 2 (3 mmol), Pd(OAc)2 (10molpercent) and 1,10-phenanthroline (15 molpercent) were combined in dry DMF (10 ml) under O2 atmosphereand stirred for 5 min (Note: DMF was dried over calcium hydride). The reaction mixture was stirred at 90oC and monitored by TLC using EtOAc-petroleum ether as the mobile phase. After completion, the reaction mixture was cooled, and water (10 ml) was added. The resulting solution was then extracted with EtOAc (3 X 20 ml). The EtOAc extract was washed with water (5 X 10 ml) and then brine (10 ml). The organic layer was dried with Na2SO4. Evaporation of EtOAc furnished the crude product, which was purified by flash chromatography on silica gel (EtOAc-Petroleum ether).
70%	With 1,10-Phenanthroline; oxygen; palladium diacetate; In N,N-dimethyl-formamide; at 90℃; for 16h;	General procedure: Uracil1 (1 mmol), the arylboronic acid 2 (3 mmol), Pd(OAc)2 (10molpercent) and 1,10-phenanthroline (15 molpercent) were combined in dry DMF (10 ml) under O2 atmosphereand stirred for 5 min (Note: DMF wasdried over calcium hydride). The reaction mixture was stirred at 90oC and monitored by TLC using EtOAc-petroleum ether as the mobilephase. After completion, the reaction mixture was cooled, and water (10 ml) wasadded. The resulting solution was then extracted with EtOAc (3 QUOTE &13;&10;&13;&10;12?"> &13;&10;&13;&10;12?"> 20 ml). TheEtOAc extract was washed with water (5 QUOTE &13;&10;&13;&10;12?"> &13;&10;&13;&10;12?"> 10 ml) and thenbrine (10 ml). The organic layer was dried with Na2SO4.Evaporation of EtOAc furnished the crude product, which was purified by flash chromatography onsilica gel (EtOAc-Petroleum ether).

Reference： [1]Tetrahedron Letters,2014,vol. 55,p. 1077 - 1081
[2]Tetrahedron Letters,2015,vol. 55,p. 1077 - 1081

61
[ 874-14-6 ]
[ 5720-05-8 ]
[ 105202-39-9 ]

Yield	Reaction Conditions	Operation in experiment
78%	With 1,10-Phenanthroline; oxygen; palladium diacetate; In N,N-dimethyl-formamide; at 90℃; for 16h;	General procedure: Uracil1 (1 mmol), the arylboronic acid 2 (3 mmol), Pd(OAc)2 (10molpercent) and 1,10-phenanthroline (15 molpercent) were combined in dry DMF (10 ml) under O2 atmosphereand stirred for 5 min (Note: DMF was dried over calcium hydride). The reaction mixture was stirred at 90oC and monitored by TLC using EtOAc-petroleum ether as the mobile phase. After completion, the reaction mixture was cooled, and water (10 ml) was added. The resulting solution was then extracted with EtOAc (3 X 20 ml). The EtOAc extract was washed with water (5 X 10 ml) and then brine (10 ml). The organic layer was dried with Na2SO4. Evaporation of EtOAc furnished the crude product, which was purified by flash chromatography on silica gel (EtOAc-Petroleum ether).
78%	With 1,10-Phenanthroline; oxygen; palladium diacetate; In N,N-dimethyl-formamide; at 90℃; for 16h;	General procedure: Uracil1 (1 mmol), the arylboronic acid 2 (3 mmol), Pd(OAc)2 (10molpercent) and 1,10-phenanthroline (15 molpercent) were combined in dry DMF (10 ml) under O2 atmosphereand stirred for 5 min (Note: DMF wasdried over calcium hydride). The reaction mixture was stirred at 90oC and monitored by TLC using EtOAc-petroleum ether as the mobilephase. After completion, the reaction mixture was cooled, and water (10 ml) wasadded. The resulting solution was then extracted with EtOAc (3 QUOTE &13;&10;&13;&10;12?"> &13;&10;&13;&10;12?"> 20 ml). TheEtOAc extract was washed with water (5 QUOTE &13;&10;&13;&10;12?"> &13;&10;&13;&10;12?"> 10 ml) and thenbrine (10 ml). The organic layer was dried with Na2SO4.Evaporation of EtOAc furnished the crude product, which was purified by flash chromatography onsilica gel (EtOAc-Petroleum ether).

Reference： [1]Tetrahedron Letters,2014,vol. 55,p. 1077 - 1081
[2]Tetrahedron Letters,2015,vol. 55,p. 1077 - 1081

62
[ 874-14-6 ]
[ 5720-07-0 ]
[ 94937-24-3 ]

Yield	Reaction Conditions	Operation in experiment
82%	With 1,10-Phenanthroline; oxygen; palladium diacetate; In N,N-dimethyl-formamide; at 90℃; for 16h;	General procedure: Uracil1 (1 mmol), the arylboronic acid 2 (3 mmol), Pd(OAc)2 (10mol%) and 1,10-phenanthroline (15 mol%) were combined in dry DMF (10 ml) under O2 atmosphereand stirred for 5 min (Note: DMF was dried over calcium hydride). The reaction mixture was stirred at 90oC and monitored by TLC using EtOAc-petroleum ether as the mobile phase. After completion, the reaction mixture was cooled, and water (10 ml) was added. The resulting solution was then extracted with EtOAc (3 X 20 ml). The EtOAc extract was washed with water (5 X 10 ml) and then brine (10 ml). The organic layer was dried with Na2SO4. Evaporation of EtOAc furnished the crude product, which was purified by flash chromatography on silica gel (EtOAc-Petroleum ether).
82%	With 1,10-Phenanthroline; oxygen; palladium diacetate; In N,N-dimethyl-formamide; at 90℃; for 16h;	General procedure: Uracil1 (1 mmol), the arylboronic acid 2 (3 mmol), Pd(OAc)2 (10mol%) and 1,10-phenanthroline (15 mol%) were combined in dry DMF (10 ml) under O2 atmosphereand stirred for 5 min (Note: DMF wasdried over calcium hydride). The reaction mixture was stirred at 90oC and monitored by TLC using EtOAc-petroleum ether as the mobilephase. After completion, the reaction mixture was cooled, and water (10 ml) wasadded. The resulting solution was then extracted with EtOAc (3 QUOTE &13;&10;&13;&10;12-"> &13;&10;&13;&10;12-"> 20 ml). TheEtOAc extract was washed with water (5 QUOTE &13;&10;&13;&10;12-"> &13;&10;&13;&10;12-"> 10 ml) and thenbrine (10 ml). The organic layer was dried with Na2SO4.Evaporation of EtOAc furnished the crude product, which was purified by flash chromatography onsilica gel (EtOAc-Petroleum ether).

Reference： [1]Tetrahedron Letters,2014,vol. 55,p. 1077 - 1081
[2]Tetrahedron Letters,2015,vol. 55,p. 1077 - 1081

63
[ 874-14-6 ]
[ 10365-98-7 ]
[ 105202-44-6 ]

Yield	Reaction Conditions	Operation in experiment
78%	With 1,10-Phenanthroline; oxygen; palladium diacetate; In N,N-dimethyl-formamide; at 90℃; for 16h;	General procedure: Uracil1 (1 mmol), the arylboronic acid 2 (3 mmol), Pd(OAc)2 (10molpercent) and 1,10-phenanthroline (15 molpercent) were combined in dry DMF (10 ml) under O2 atmosphereand stirred for 5 min (Note: DMF was dried over calcium hydride). The reaction mixture was stirred at 90oC and monitored by TLC using EtOAc-petroleum ether as the mobile phase. After completion, the reaction mixture was cooled, and water (10 ml) was added. The resulting solution was then extracted with EtOAc (3 X 20 ml). The EtOAc extract was washed with water (5 X 10 ml) and then brine (10 ml). The organic layer was dried with Na2SO4. Evaporation of EtOAc furnished the crude product, which was purified by flash chromatography on silica gel (EtOAc-Petroleum ether).
78%	With 1,10-Phenanthroline; oxygen; palladium diacetate; In N,N-dimethyl-formamide; at 90℃; for 16h;	General procedure: Uracil1 (1 mmol), the arylboronic acid 2 (3 mmol), Pd(OAc)2 (10molpercent) and 1,10-phenanthroline (15 molpercent) were combined in dry DMF (10 ml) under O2 atmosphereand stirred for 5 min (Note: DMF wasdried over calcium hydride). The reaction mixture was stirred at 90oC and monitored by TLC using EtOAc-petroleum ether as the mobilephase. After completion, the reaction mixture was cooled, and water (10 ml) wasadded. The resulting solution was then extracted with EtOAc (3 QUOTE &13;&10;&13;&10;12?"> &13;&10;&13;&10;12?"> 20 ml). TheEtOAc extract was washed with water (5 QUOTE &13;&10;&13;&10;12?"> &13;&10;&13;&10;12?"> 10 ml) and thenbrine (10 ml). The organic layer was dried with Na2SO4.Evaporation of EtOAc furnished the crude product, which was purified by flash chromatography onsilica gel (EtOAc-Petroleum ether).

Reference： [1]Tetrahedron Letters,2014,vol. 55,p. 1077 - 1081
[2]Tetrahedron Letters,2015,vol. 55,p. 1077 - 1081

64
[ 874-14-6 ]
[ 1679-18-1 ]
[ 1420466-92-7 ]

Yield	Reaction Conditions	Operation in experiment
69%	With 1,10-Phenanthroline; oxygen; palladium diacetate; In N,N-dimethyl-formamide; at 90℃; for 16h;	General procedure: Uracil1 (1 mmol), the arylboronic acid 2 (3 mmol), Pd(OAc)2 (10molpercent) and 1,10-phenanthroline (15 molpercent) were combined in dry DMF (10 ml) under O2 atmosphereand stirred for 5 min (Note: DMF was dried over calcium hydride). The reaction mixture was stirred at 90oC and monitored by TLC using EtOAc-petroleum ether as the mobile phase. After completion, the reaction mixture was cooled, and water (10 ml) was added. The resulting solution was then extracted with EtOAc (3 X 20 ml). The EtOAc extract was washed with water (5 X 10 ml) and then brine (10 ml). The organic layer was dried with Na2SO4. Evaporation of EtOAc furnished the crude product, which was purified by flash chromatography on silica gel (EtOAc-Petroleum ether).
69%	With 1,10-Phenanthroline; oxygen; palladium diacetate; In N,N-dimethyl-formamide; at 90℃; for 16h;	General procedure: Uracil1 (1 mmol), the arylboronic acid 2 (3 mmol), Pd(OAc)2 (10molpercent) and 1,10-phenanthroline (15 molpercent) were combined in dry DMF (10 ml) under O2 atmosphereand stirred for 5 min (Note: DMF wasdried over calcium hydride). The reaction mixture was stirred at 90oC and monitored by TLC using EtOAc-petroleum ether as the mobilephase. After completion, the reaction mixture was cooled, and water (10 ml) wasadded. The resulting solution was then extracted with EtOAc (3 QUOTE &13;&10;&13;&10;12?"> &13;&10;&13;&10;12?"> 20 ml). TheEtOAc extract was washed with water (5 QUOTE &13;&10;&13;&10;12?"> &13;&10;&13;&10;12?"> 10 ml) and thenbrine (10 ml). The organic layer was dried with Na2SO4.Evaporation of EtOAc furnished the crude product, which was purified by flash chromatography onsilica gel (EtOAc-Petroleum ether).

Reference： [1]Tetrahedron Letters,2014,vol. 55,p. 1077 - 1081
[2]Tetrahedron Letters,2015,vol. 55,p. 1077 - 1081

65
[ 874-14-6 ]
[ 2926-29-6 ]
[ 85199-75-3 ]

Reference： [1]Science,2019,vol. 365,p. 360 - 366
[2]Chemical Communications,2016,vol. 52,p. 2493 - 2496
[3]Heterocycles,2014,vol. 89,p. 1159 - 1171

66
[ 874-14-6 ]
[ 6825-71-4 ]
[ 1466565-59-2 ]

Yield	Reaction Conditions	Operation in experiment
79%	With sodium ethanolate; In ethanol; at 90℃;	To a solution of sodium ethoxide in EtOH (0.49 N, 100 mL) were added ethyl 3,5- diamino-lH-pyrazole-4-carboxylate (2.08g, 0.012 mol), followed by solid <strong>[874-14-6]1,3-dimethyluracil</strong> (1.7 g, 0.012mol) and then the reaction mixture was stirred overnight at 90 C. The reaction mixture was cooled to r.t, filtered to give the title compound as a pink solid (2.1 g, 79%). NMR (300MHz, OMSO-de): delta (ppm) 11.30 (brs, 1H), 8.23 (d, J= 7.86 Hz, 1H), 5.93 (brs, 2H), 5.89 (d, J= 7.83 Hz, 1H), 4.26 (q, J= 7.08 Hz, 2H), 1.28 (t, J= 7.08 Hz, 3H).
79%	With sodium ethanolate; In ethanol; at 90℃;	To a solution of sodium ethoxide in ethanol (0.49 M, 100 mL)3,5-Diamino-1 -hydro-pyrazole-4-carboxylic acid ethyl ester (2.08 g, 0.012 mol)<strong>[874-14-6]1,3-dimethyluracil</strong> (1.7 g, 0.012 mol),The reaction was stirred at 90 C overnight.The resulting reaction mixture was cooled to room temperature and filtered to give the title compound as a pink solid (2.1 g, 79%).
38.3%	With sodium ethanolate; In ethanol; at 90℃; for 9h;	To a solution of fresh prepared sodium ethoxide (0.50 M, 2.35 L, 4.00 eq. ) in ethanol (200 mL) was added A-3-3 (50.0 g, 294 mmol, 1.00 eq. ), then A-3-3A (41.2 g, 294 mmol, 1.00 eq. ) was added. The mixture was stirred at 90 C for 9 hours. Filtered and filter cake was washed with ethanol (100 mL) to give the A-3-4 (25.0 g, 113 mmol, yield = 38.3%) as a brown solid. 1H NMR (400 MHz, DMSO-d6) delta = 7.71 (d, 7=7.2 Hz, IH), 5.57 - 5.46 (m, 3H), 4.15 (q, 7=7.2 Hz, 2H), 1.25 (t, 7=7.2 Hz, 3H).

18.4 g	With sodium ethanolate; In ethanol; at 90℃; for 12h;	Sodium ethoxide (33.2g) at room temperatureEthanol solution (500mL)3,5-Diamino-1H-pyrazole-4-carboxylic acid ethyl ester (20.8 g) was added in sequence.1,3-Dimethylpyrimidine-2,4(1H,3H)-dione (17.0 g).After the completion of heating to 90 C reaction12 hours.After the reaction is completed,The pH was adjusted to pH 7 with 1N hydrochloric acid at room temperature.Collect solids,Ethanol wash,Dry to give the title compound (18.4 g).
18.4 g	With sodium ethanolate; In ethanol; at 90℃; for 12h;	To a solution of sodium ethoxide (33.2 g) in ethanol (500 mL) were sequentially added ethyl 3,5-diamino-1H-pyrazole-4-carboxylate (20.8 g) and 1,3-dimethyl pyrimidine-2,4(1H,3H)-dione (17.0 g) at room temperature. Then, the resulting mixture was warmed to 90C and reacted for 12 hours. After the completion of the reaction, the mixture was cooled to room temperature, and adjusted to pH = 7 with 1N hydrochloric acid solution. The solid was collected and rinsed with ethanol to afford the title compound (18.4 g). 1H NMR (400 MHz, DMSO-d6) delta 11.17 (brs, 1H), 8.24 (d, J = 8.0 Hz, 1H), 5.93 (s, 2H), 5.90 (d, J = 8.0 Hz, 1H), 4.26 (q, J = 7.2 Hz, 2H), 1.27 (t, J = 7.2 Hz, 3H). m/z=223[M+1]+.

Reference： [1]Patent: WO2015/73267,2015,A1 .Location in patent: Paragraph 368
[2]Patent: CN104650092,2017,B .Location in patent: Paragraph 0684-0685
[3]Patent: WO2019/23417,2019,A1 .Location in patent: Paragraph 0250; 0253
[4]Patent: CN108003161,2018,A .Location in patent: Paragraph 0849; 0859-0861
[5]Patent: EP3533796,2019,A1 .Location in patent: Paragraph 0113; 0118; 0119

67
[ 75-77-4 ]
[ 119-61-9 ]
[ 874-14-6 ]
6-(diphenyl((trimethylsilyl)oxy)methyl)-1,3-dimethyldihydropyrimidine-2,4(1H,3H)-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With tetrabutylammonium perchlorate; triethylamine; In tetrahydrofuran; at 20℃;Inert atmosphere; Electrochemical reaction;	A 0.3M solution of Bu4NClO4 in THF (15 mL) was placed in thecathodic chamber of a divided cell (40 mL beaker, 3 cm diameter, 6 cm height)equipped with a lead cathode (5 X 5 cm2), a platinum anode (2 X 1 cm2),and a ceramic cylindrical diaphragm (1.5 cm diameter). A 0.3 M solution of Et4NOTsin DMF (4 mL) was placed in the anodic chamber (inside the diaphragm). 1,3-Dimethylpyrimidine-2,4(1H,3H)-dione(1a) (140 mg, 1.0 mmol), benzophenone (2a) (368mg, 2.0 mmol), TMSCl (0.64 mL, 5 mmol), and TEA (0.70 mL, 5 mmol) were added tothe cathodic chamber. After 400 C of electricity was passed at a constantcurrent of 200 mA at room temperature under nitrogen atmosphere, the catholytewas evaporated in vacuo. The residue was dissolved in diethyl ether (20 mL)and insoluble solid was filtered off. After removal of the solvent in vacuo, the residue was purified by column chromatography on silica gel(hexanes-EtOAc) to give 3a (305 mg) in 77percent yield.

Reference： [1]Tetrahedron Letters,2015,vol. 56,p. 4599 - 4602
[2]Journal of Organic Chemistry,2016,vol. 81,p. 5101 - 5119

68
[ 75-77-4 ]
[ 874-14-6 ]
[ 1210-35-1 ]
1,3-dimethyl-6-(5-((trimethylsilyl)oxy)-10,11-dihydro-5H-dibenzo[a,d][7]annulen-5-yl)dihydropyrimidine-2,4(1H,3H)-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With tetrabutylammonium perchlorate; triethylamine; In tetrahydrofuran; at 20℃;Inert atmosphere; Electrochemical reaction;	General procedure: A 0.3M solution of Bu4NClO4 in THF (15 mL) was placed in thecathodic chamber of a divided cell (40 mL beaker, 3 cm diameter, 6 cm height)equipped with a lead cathode (5 X 5 cm2), a platinum anode (2 X 1 cm2),and a ceramic cylindrical diaphragm (1.5 cm diameter). A 0.3 M solution of Et4NOTsin DMF (4 mL) was placed in the anodic chamber (inside the diaphragm). 1,3-Dimethylpyrimidine-2,4(1H,3H)-dione(1a) (140 mg, 1.0 mmol), benzophenone (2a) (368mg, 2.0 mmol), TMSCl (0.64 mL, 5 mmol), and TEA (0.70 mL, 5 mmol) were added tothe cathodic chamber. After 400 C of electricity was passed at a constantcurrent of 200 mA at room temperature under nitrogen atmosphere, the catholytewas evaporated in vacuo. The residue was dissolved in diethyl ether (20 mL)and insoluble solid was filtered off. After removal of the solvent in vacuo, the residue was purified by column chromatography on silica gel(hexanes-EtOAc) to give 3a (305 mg) in 77percent yield.

Reference： [1]Tetrahedron Letters,2015,vol. 56,p. 4599 - 4602
[2]Journal of Organic Chemistry,2016,vol. 81,p. 5101 - 5119

69
[ 75-77-4 ]
[ 874-14-6 ]
[ 611-70-1 ]
1,3-dimethyl-6-(2-methyl-1-phenyl-1-((trimethylsilyl)oxy)propyl)dihydropyrimidine-2,4(1H,3H)-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With tetrabutylammonium perchlorate; triethylamine; In tetrahydrofuran; at 20℃;Inert atmosphere; Electrochemical reaction;	General procedure: A 0.3M solution of Bu4NClO4 in THF (15 mL) was placed in thecathodic chamber of a divided cell (40 mL beaker, 3 cm diameter, 6 cm height)equipped with a lead cathode (5 X 5 cm2), a platinum anode (2 X 1 cm2),and a ceramic cylindrical diaphragm (1.5 cm diameter). A 0.3 M solution of Et4NOTsin DMF (4 mL) was placed in the anodic chamber (inside the diaphragm). 1,3-Dimethylpyrimidine-2,4(1H,3H)-dione(1a) (140 mg, 1.0 mmol), benzophenone (2a) (368mg, 2.0 mmol), TMSCl (0.64 mL, 5 mmol), and TEA (0.70 mL, 5 mmol) were added tothe cathodic chamber. After 400 C of electricity was passed at a constantcurrent of 200 mA at room temperature under nitrogen atmosphere, the catholytewas evaporated in vacuo. The residue was dissolved in diethyl ether (20 mL)and insoluble solid was filtered off. After removal of the solvent in vacuo, the residue was purified by column chromatography on silica gel(hexanes-EtOAc) to give 3a (305 mg) in 77percent yield.

Reference： [1]Tetrahedron Letters,2015,vol. 56,p. 4599 - 4602
[2]Journal of Organic Chemistry,2016,vol. 81,p. 5101 - 5119

70
[ 874-14-6 ]
[ 1225387-53-0 ]
[ 1224944-43-7 ]

Yield	Reaction Conditions	Operation in experiment
96%	With sodium ethanolate; In ethanol; at 75℃;Inert atmosphere;	10405] A solution of 1H-pyrazol-5-amine and 1,3-dimeth- ylpyrimidine-2,4(1H,3H)-dione (1.05 equiv.) were charged to a round bottom flask outfitted with a mechanical stirrer,steam pot, a reflux condenser, a J-Kem temperature probe and an N2 adaptor for positive N2 pressure control. Under mechanical stirring the solids were suspended with 4 vol. (4 mL/g) of absolute EtOR under a nitrogen atmosphere, then charged with 2.1 equivalents of NaOEt (21 wt percent solution in EtOR), and followed by line-rinse with 1 vol. (1 mL/g) of absolute EtOR. The slurry was warmed to about 75° Celsius and stirred at gentle reflux until less than 1 .5 area percent of 1H-pyrazol-5-amine was observed by TRK1PM1 HPLC tofollow the progression of the reaction using 20 tL of slurry diluted in 4 mE deionized water and 5 tE injection at 220 mm10406] After 1 additional hour, the mixture was charged with 2.5 vol. (2.5 mE/g) of heptane and then refluxed at 70° Celsius for 1 hout The slurry was then cooled to room temperature overnight. The solid was collected by filtrationa tabletop funnel and polypropylene filter cloth. The reactor was rinsed and charged atop the filter cake with 4 vol. (4 mE/g) of heptane with the cake pulled and the solids being transferred to tared drying trays and oven-dried at 45° Celsius under high vacuum until their weight was constant. Pale yellow solid sodium pyrazolo[1 ,5-a] -pyrimidin-5-olate was obtained in 93-96percent yield (corrected) and larger than 99.5 area percent observed by HPEC (1 mgmE dilution in deionized water, TRK1PM1 at 220 nm).
	With sodium ethanolate; In ethanol; at 75℃;Inert atmosphere;	A solution of lH-pyrazol-5-amine and 1,3-dimethylpyrimidine-2,4(lH,3H)-dione (1.05 equiv.) were charged to a round bottom flask outfitted with a mechanical stirrer, a steam pot, a reflux condenser, a J-Kem temperature probe and an N2 adaptor for positive N2 pressure control. Under mechanical stirring the solids were suspended with 4 vol. (4 mL/g) of absolute EtOH under a nitrogen atmosphere, then charged with 2.1 equivalents of NaOEt (21 wtpercent solution in EtOH), and followed by line-rinse with 1 vol. (1 mL/g) of absolute EtOH. The slurry was warmed to about 75° Celsius and stirred at gentle reflux until less than 1.5 area percent of 1H-pyrazol-5-amine was observed by TRK1PM1 E1PLC to follow the progression of the reaction using 20 pL of slurry diluted in 4 mL deionized water and 5 pL injection at 220 nm. After 1 additional hour, the mixture was charged with 2.5 vol. (2.5 mL/g) of heptane and then refluxed at 70° Celsius for 1 hour. The slurry was then cooled to room temperature overnight. The solid was collected by filtration on a tabletop funnel and polypropylene filter cloth. The reactor was rinsed and charged atop the filter cake with 4 vol. (4mL/g) of heptane with the cake pulled and the solids being transferred to tared drying trays and oven-dried at 45° Celsius under high vacuum until their weight was constant. Pale yellow solid sodium pyrazolo[l,5-a]-pyrimidin-5-olate was obtained in 93-96percent yield (corrected) and larger than 99.5 area percent observed by HPLC (1 mg/mL dilution in deionized water, TRK1PM1 at 220 nm).

Reference： [1]Patent: US2017/281632,2017,A1 .Location in patent: Paragraph 0405; 0406
[2]Patent: US2016/137654,2016,A1 .Location in patent: Paragraph 0237-0238

71
[ 874-14-6 ]
[ 3278-34-0 ]
[ 65396-90-9 ]

Yield	Reaction Conditions	Operation in experiment
25%	With dilauryl peroxide; In 1,2-dichloro-ethane; at 85℃;Microwave irradiation;	General procedure: A solution of the corresponding xanthate (2 mmol) and Imidazo[1,2-a]pyridines (1 mmol) in 1,2-Dichloroethane [0.1 M] was irradiated in a Biotage microwave at 85 C, then, dilauroyl peroxide (2 equiv) was added portionwise (0.28 equiv/15min), the organic solvent was removed under reduced pressure and the crude residue was purified by flash chromatography.

Reference： [1]Tetrahedron Letters,2017,vol. 58,p. 1326 - 1329

72
[ 874-14-6 ]
[ 369-57-3 ]
[ 55377-22-5 ]

Yield	Reaction Conditions	Operation in experiment
Ca. 78.4%	With copper dichloride; In dimethyl sulfoxide; at 20℃; for 9h;	A solution of 14.1 g (0.1 mol) of <strong>[874-14-6]1,3-dimethyluracil</strong> and 2.0 g (0.02 mol) of cuprous chloride were added to 100 mL of DMSO,38.2 g (0.2 mol) of the phenyl diazonium tetrafluoroborate in the above Example 1 was added portionwise with stirring at room temperature,1h plus finished,After joining,Stir at room temperature for 8 h.Reaction is completed,Add water 150mL,Extracted with ethyl acetate 150 mL x 2,The ethyl acetate layer was dried over anhydrous sodium sulfate,The solvent is distilled off,95percent (v / v) ethanol to give 16.7 g of white crystals,Yield of about 78.4percent

Reference： [1]Patent: CN106349170,2017,A .Location in patent: Paragraph 0044; 0045; 0046; 0047; 0048; 0049; 0050-0053

73
[ 874-14-6 ]
[ 355-43-1 ]
1,3-dimethyl-5-(perfluorohexyl)pyrimidine-2,4(1H,3H)-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With tris(2,2'-bipyridyl)ruthenium dichloride; caesium carbonate; In dimethyl sulfoxide; at 20℃; for 24h;Irradiation; Inert atmosphere; Schlenk technique; Green chemistry;Catalytic behavior;	General procedure: To a 25 mL of Schlenk tube equipped with a Teflon septum were added Ru(bpy)3Cl2 (1.5 mg, 0.5 molpercent), Cs2CO3 (130 mg, 1.0 equiv) and 1 (0.4 mmol, 1.0 equiv) followed by DMSO 3.0 mL) with stirring. Perfluoroalkyl iodine (2.0 equiv.) was then added subsequently under Ar. The Schlenk tube was screw capped and the reaction was then under irradiated with a 12 W blue LEDs (460 nm?470 nm). After stirring for 24 h, the reaction mixture was diluted with ethyl acetate, washed with brine, the organic phases were collected and dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified with silica gel chromatography to provide pure product.

Reference： [1]Chinese Chemical Letters,2017,vol. 28,p. 1751 - 1754

74
[ 874-14-6 ]
[ 423-39-2 ]
[ 71623-68-2 ]

Yield	Reaction Conditions	Operation in experiment
87%	With tris(2,2'-bipyridyl)ruthenium dichloride; caesium carbonate; In dimethyl sulfoxide; at 20℃; for 24h;Irradiation; Inert atmosphere; Schlenk technique; Green chemistry;	General procedure: To a 25 mL of Schlenk tube equipped with a Teflon septum were added Ru(bpy)3Cl2 (1.5 mg, 0.5 molpercent), Cs2CO3 (130 mg, 1.0 equiv) and 1 (0.4 mmol, 1.0 equiv) followed by DMSO 3.0 mL) with stirring. Perfluoroalkyl iodine (2.0 equiv.) was then added subsequently under Ar. The Schlenk tube was screw capped and the reaction was then under irradiated with a 12 W blue LEDs (460 nm?470 nm). After stirring for 24 h, the reaction mixture was diluted with ethyl acetate, washed with brine, the organic phases were collected and dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified with silica gel chromatography to provide pure product.

Reference： [1]Chinese Chemical Letters,2017,vol. 28,p. 1751 - 1754
[2]Patent: CN110642831,2020,A .Location in patent: Paragraph 0096-0100
[3]Chemical Communications,2020,vol. 56,p. 1815 - 1818
[4]Chemical Communications,2018,vol. 54,p. 13662 - 13665

75
[ 874-14-6 ]
3-[dimethyl(4-fluorophenyl)silyl]-1-propanol [ No CAS ]
[ 7033-39-8 ]
5-(4-fluorophenyl)-1,3-dimethyluracil [ No CAS ]

Reference： [1]Chemistry - A European Journal,2016,vol. 22,p. 12641 - 12645

76
[ 874-14-6 ]
[ 5335-87-5 ]
5-[(4-methoxyphenyl)thio]-1,3-dimethylpyrimidine-2,4(1H,3H)-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With dipotassium peroxodisulfate; iodine; In acetonitrile; at 60℃;	General procedure: An 8 mL oven-dried scintillation vial equipped with a magnetic stir bar was charged with a mixture of 4-quinolone or uracil (0.50 mmol, 1.0 equiv), disulfide or thiol (0.75 mmol, 1.5 equiv), molecular iodine (I2) (128 mg, 0.50 mmol, 1.0 equiv), K2S2O8 (1.00-1.50 mmol, 2.0-3.0 equiv), and acetonitrile (CH3CN) (1 mL). The vial was capped, and the reaction mixture was stirred at 60 or 80 C for 12-16 h. Upon completion, saturated Na2S2O3 (5 mL) and distilled deionized H2O (10 mL) was added, and the mixture was extracted with ethyl acetate (3 x 25 mL). The combined organic layer was washed with saturated NaCl, dried over anhydrous Na2SO4, and concentrated in vacuo. The crude product was purified by SiO2 column chromatography to afford the desired thioether products.

Reference： [1]European Journal of Organic Chemistry,2019,vol. 2019,p. 2759 - 2766
[2]Tetrahedron,2019,vol. 75

77
[ 874-14-6 ]
[ 1142-19-4 ]
5-[(4-chlorophenyl)thio]-1,3-dimethylpyrimidine-2,4(1H,3H)-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With dipotassium peroxodisulfate; iodine; In acetonitrile; at 60℃;	General procedure: An 8 mL oven-dried scintillation vial equipped with a magnetic stir bar was charged with a mixture of 4-quinolone or uracil (0.50 mmol, 1.0 equiv), disulfide or thiol (0.75 mmol, 1.5 equiv), molecular iodine (I2) (128 mg, 0.50 mmol, 1.0 equiv), K2S2O8 (1.00-1.50 mmol, 2.0-3.0 equiv), and acetonitrile (CH3CN) (1 mL). The vial was capped, and the reaction mixture was stirred at 60 or 80 C for 12-16 h. Upon completion, saturated Na2S2O3 (5 mL) and distilled deionized H2O (10 mL) was added, and the mixture was extracted with ethyl acetate (3 x 25 mL). The combined organic layer was washed with saturated NaCl, dried over anhydrous Na2SO4, and concentrated in vacuo. The crude product was purified by SiO2 column chromatography to afford the desired thioether products.

Reference： [1]Tetrahedron,2019,vol. 75
[2]European Journal of Organic Chemistry,2019,vol. 2019,p. 2759 - 2766

78
[ 874-14-6 ]
[ 135-57-9 ]
N-{2-[(1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-thio]phenyl}benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With dipotassium peroxodisulfate; iodine; In acetonitrile; at 60℃;	General procedure: An 8 mL oven-dried scintillation vial equipped with a magnetic stir bar was charged with a mixture of 4-quinolone or uracil (0.50 mmol, 1.0 equiv), disulfide or thiol (0.75 mmol, 1.5 equiv), molecular iodine (I2) (128 mg, 0.50 mmol, 1.0 equiv), K2S2O8 (1.00-1.50 mmol, 2.0-3.0 equiv), and acetonitrile (CH3CN) (1 mL). The vial was capped, and the reaction mixture was stirred at 60 or 80 C for 12-16 h. Upon completion, saturated Na2S2O3 (5 mL) and distilled deionized H2O (10 mL) was added, and the mixture was extracted with ethyl acetate (3 x 25 mL). The combined organic layer was washed with saturated NaCl, dried over anhydrous Na2SO4, and concentrated in vacuo. The crude product was purified by SiO2 column chromatography to afford the desired thioether products.

Reference： [1]Tetrahedron,2019,vol. 75
[2]European Journal of Organic Chemistry,2019,vol. 2019,p. 2759 - 2766

79
[ 874-14-6 ]
[ 73178-07-1 ]
(4-chlorophenyl)(1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)iodonium tosylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	In 2,2,2-trifluoroethanol; at 20℃; for 24h;	To a solution of <strong>[874-14-6]1,3-dimethyluracil</strong> 1a (0.20 mmol) in 2,2,2-trifluoroethanol (TFE) (3 mL),(4-chlorophenyl)(hydroxy)iodonium tosylate 2f (0.20 mmol) was added and it was stirred at room temperature. After completion of the reaction, the solvent was removed under vacuum. The product wasthen precipitated by the addition of Et2O with stirring. The precipitate was filtered to giveuracil-iodonium(III) salt 3f as white powder.
98%	In 2,2,2-trifluoroethanol; at 20℃;	To a solution of <strong>[874-14-6]1,3-dimethyluracil</strong> 1a (0.20 mmol) in 2,2,2-trifluoroethanol (TFE) (3 mL), (4-chlorophenyl)(hydroxy)iodonium tosylate 2f (0.22 mmol) was added and it was stirred at room temperature. After completion of the reaction, the solvent was removed under vacuum. The product was then precipitated by the addition of Et2O with stirring. The precipitate was filtered to give uracil-iodonium(III) salt 3af-OTs as a white powder.(4-Chlorophenyl)(1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)iodonium tosylate (3af-OTs).A white powder, m.p. 186-187 C. IR (KBr) cm-1: 1715, 1656, 1615, 1214, 1169, 997, 682. 1H-NMR(600 MHz, CD3OD) delta 2.37 (s, 3H), 3.33 (s, 3H), 3.47 (s, 3H), 7.23 (d, 2H, J = 7.8 Hz), 7.54 (d, 2H, J = 9.0Hz), 7.69 (d, 2H, J = 7.8 Hz), 8.12 (d, 2H, J = 9.0 Hz), 8.92 (s, 1H) ppm. 13C-NMR (150 MHz, MeOD) delta19.9, 28.4, 36.9, 88.2, 112.3, 125.5, 128.4, 131.6, 136.7, 139.0, 140.3, 142.2, 150.9, 154.5, 159.4 ppm. HRMS(FAB): Calcd. for C12H11ClIN2O2 [M - OTs]+: 376.9548, found: 376.9569.

Reference： [1]Heterocycles,2018,vol. 97,p. 1248 - 1256
[2]Molecules,2019,vol. 24

80
[ 874-14-6 ]
[ 6973-73-5 ]
(4-chlorophenyl)(1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)iodonium perchlorate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With perchloric acid; In 2,2,2-trifluoroethanol; at 20℃; for 24h;	General procedure: To a solution of <strong>[874-14-6]1,3-dimethyluracil</strong> 1a (0.20 mmol) in 2,2,2-trifluoroethanol (TFE) (3 mL),(4-chlorophenyl)(hydroxy)iodonium tosylate 2f (0.20 mmol) was added and it was stirred at room temperature. After completion of the reaction, the solvent was removed under vacuum. The product wasthen precipitated by the addition of Et2O with stirring. The precipitate was filtered to giveuracil-iodonium(III) salt 3f as white powder.
68%	With perchloric acid; In 2,2,2-trifluoroethanol; at 20℃;	General procedure: To a solution of <strong>[874-14-6]1,3-dimethyluracil</strong> 1a (0.20 mmol) in 2,2,2-trifluoroethanol (TFE) (3 mL), (4-chlorophenyl)(hydroxy)iodonium tosylate 2f (0.22 mmol) was added and it was stirred at room temperature. After completion of the reaction, the solvent was removed under vacuum. The product was then precipitated by the addition of Et2O with stirring. The precipitate was filtered to give uracil-iodonium(III) salt 3af-OTs as a white powder.

Reference： [1]Heterocycles,2018,vol. 97,p. 1248 - 1256
[2]Molecules,2019,vol. 24

81
[ 874-14-6 ]
[ 1493-13-6 ]
[ 6973-73-5 ]
(4-chlorophenyl)(1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)iodonium triflate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	In acetonitrile; at 20℃; for 3h;	General procedure: To a stirred solution of <strong>[874-14-6]1,3-dimethyluracil</strong> 1a (0.50 mmol) and 4-chloroiodobenzene diacetate 2e (0.55 mmol) in dichloromethane or acetonitrile (2 mL), a solution of trifluoromethanesulfonic acid (ca. 150 mg, 1.0 mmol, 2 equiv) in acetonitrile (1 mL) was added dropwise at room temperature, and the resulting slightly colored solution was stirred for 3 h. After addition of methanol (~2 mL), the solvents were removed under reduced pressure. The residue was then treated with diethyl ether with stirring for precipitation of the iodonium(III) salt. The precipitate was filtered and dried in vacuo to give a pure iodonium(III) salt in powder form.

Reference： [1]Molecules,2019,vol. 24
[2]Heterocycles,2018,vol. 97,p. 1248 - 1256

82
[ 874-14-6 ]
[ 1203705-55-8 ]
(2-bromopyrazolo[1,5-a]pyrimidin-5-yl)oxysodium [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
38%	With sodium; at 80.0℃; for 3.0h;	To a solution of Na (7.10 g, 309 mmol) in EtOH (125 mL) was added <strong>[1203705-55-8]3-bromo-1H-pyrazol-5-amine</strong> (5.00 g, 30.9 mmol, CAS1203705-55-8) and 1,3-dimethylpyrimidine-2,4-dione (4.33 g, 30.9 mmol, CAS874-14-6). The reaction mixture was stirred at 80 C. for 3 hours. On completion, the mixture was cooled to 0-5 C., then filtered. The filter cake was washed with cold EtOH, and dried in vacuo to give the title compound (2.80 g, 38% yield) as a yellow solid. 1H NMR (400 MHz, D2O) delta 8.02 (d, J=7.6 Hz, 1H), 5.98 (d, J=7.6 Hz, 1H), 5.85 (s, 1H).

Reference： [1]Patent: US2019/192668,2019,A1 .Location in patent: Paragraph 2542; 2543

83
[ 874-14-6 ]
[ 637-87-6 ]
[ 1493-13-6 ]
(4-chlorophenyl)(1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)iodonium triflate [ No CAS ]