[ CAS No. 6825-71-4 ] {[proInfo.proName]}

Name: 6825-71-4|Ethyl 3,5-diamino-1H-pyrazole-4-carboxylate|95%
Brand: Ambeed
SKU: A203663
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Quality Control of [ 6825-71-4 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 6825-71-4 ]

CAS No. :	6825-71-4	MDL No. :	MFCD04070845
Formula :	C₆H₁₀N₄O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	HRAWNPOJGRIJSB-UHFFFAOYSA-N
M.W :	170.17	Pubchem ID :	4126248
Synonyms :

Calculated chemistry of [ 6825-71-4 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.33
Num. rotatable bonds :	3
Num. H-bond acceptors :	3.0
Num. H-bond donors :	3.0
Molar Refractivity :	43.48
TPSA :	107.02 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) :	-7.13 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.87
Log Po/w (XLOGP3) :	0.29
Log Po/w (WLOGP) :	-0.23
Log Po/w (MLOGP) :	-0.31
Log Po/w (SILICOS-IT) :	-0.29
Consensus Log Po/w :	0.07

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.19
Solubility :	11.0 mg/ml ; 0.0649 mol/l
Class :	Very soluble
Log S (Ali) :	-2.1
Solubility :	1.35 mg/ml ; 0.00795 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-0.99
Solubility :	17.3 mg/ml ; 0.102 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.83

Safety of [ 6825-71-4 ]

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 [ 6825-71-4 ]

* 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 [ 6825-71-4 ]
Downstream synthetic route of [ 6825-71-4 ]

[ 6825-71-4 ] Synthesis Path-Upstream 1~5

1
[ 49765-05-1 ]
[ 6825-71-4 ]

Yield	Reaction Conditions	Operation in experiment
74.2%	With hydrazine In water; N,N-dimethyl-formamide at 100℃; for 2 h;	To a solution of (Z)-ethyl 3-amino-4,4,4-trichloro-2-cyanobut-2-enoate (82.34 g, 319.77 mmol) in DMF (250 mL) was added a solution of hydrazine in water (50percent [w/w], 46.08 g, 718.88 mmol). The reaction mixture was stirred at 100 °C for 2 h and concentrated in vacuo. The residue was diluted with DCM (100 mL), and the resulting mixture was stood overnight. The solid was collected by Alteration, and then washed with DCM (50 mL x 3) to give the title compound as a pale yellow solid (40.40 g, 74.2percent).MS (ESI, pos. ion) m/z: 171.0 [M+H]⁺;^lH NMR (400 MHz, OMSO-ds): δ (ppm) 5.35 (s, 4H), 4.14 (q, J = 7.12 Hz, 2H), 1.24 (t, J =7.12 Hz, 3H).
74.2%	With hydrazine hydrate In N,N-dimethyl-formamide at 100℃; for 2 h;	To a solution of ethyl (Z) -3-amino-4,4,4-trichloro-2-cyano-2-enebutyrate (82.34 g, 319.77 mmol)In N, N-dimethylformamide (250 mL)Aqueous solution of hydrazine hydrate (50percent [w / w], 46.08 g, 718.88 mmol) was added to the solution,After the resultant reaction solution was stirred at 100 ° C for 2 hours,Concentrate under reduced pressure. The resulting residue was diluted with dichloromethane (100 mL) and the resulting mixture was allowed to stand overnight. Filtration, collection of the solid and washing with dichloromethane (50 mL x 3) yielded the title compound as a pale yellow solid (40.40 g, 74.2percent).
67%	With hydrazine hydrate In N,N-dimethyl-formamide at 100℃; for 1.5 h;	Ethyl (Z)-3-amino-4,4,4-trichloro-2-cyano-crotonate (92.1 g)Slow in DMF solution (250mL)Slowly add hydration hydrazine (50g),The reaction mixture was heated to 100°C and stirred for 1.5 hours.Concentrate to remove the solvent,The residue is slurried with dichloromethane.Then let it stand overnight.Collect the solid by suction,Dichloromethane elution,dry,The title compound was obtained (41.0 g, 67percent yield).

58%

With hydrazine In N,N-dimethyl-formamide at 100℃; for 1 h;

ethyl 3 ,5-diamino- 1 H-pyrazole-4-carboxylateHydrazine (2.19 mL, 70 mmol) was added to (Z)-ethyl 3-amino-4,4,4-trichloro-2-cyanobut-2- enoate (15.0 g, 58 mmol) in DMF (50 mL). The reaction mixture was heated to 100 ⁰C for 1 hr, then cooled to room temperature. The DMF was removed in vacuo, then the residue was slurried in a 95:5 mixture of DCM: 2M methanolic ammonia solution. The resulting precipitate was filtered off, washed with a 95:5 mixture of DCM:MeOH, and dried under vacuum to afford 5.72g (58percent) of ethyl 3,5-diamino-lH-pyrazole-4-carboxylate as a white solid. ¹H NMR (400 MHz, DMSO) δ 10.53 (s, IH), 5.28 (br, 4H), 4.14 (q, /= 7.1, 2H), 1.33 - 1.15 (t, J = 7.1, 3H).

Reference： [1] Patent: WO2015/73267, 2015, A1, . Location in patent: Paragraph 317; 367
[2] Patent: CN104650092, 2017, B, . Location in patent: Paragraph 0463-0464; 0469-0470
[3] Patent: CN108003161, 2018, A, . Location in patent: Paragraph 0849; 0855-0857
[4] Patent: WO2011/3065, 2011, A2, . Location in patent: Page/Page column 110

2
[ 105-56-6 ]
[ 6825-71-4 ]

Reference： [1] Patent: WO2011/3065, 2011, A2,
[2] Patent: WO2015/73267, 2015, A1,
[3] Patent: US2015/336962, 2015, A1,
[4] Patent: WO2017/48702, 2017, A1,
[5] Patent: CN104650092, 2017, B,
[6] Patent: CN108003161, 2018, A,

3
[ 22071-00-7 ]
[ 6825-71-4 ]

Reference： [1] Patent: US2015/336962, 2015, A1, . Location in patent: Paragraph 0478

4
[ 121020-70-0 ]
[ 6825-71-4 ]

Reference： [1] Patent: WO2017/48702, 2017, A1,

5
[ 102-52-3 ]
[ 6825-71-4 ]
[ 1260169-02-5 ]

Yield	Reaction Conditions	Operation in experiment
58.1%	at 100℃; for 14 h;	To a solution of ethyl 3,5-diamino-lH-pyrazole-4-carboxylate (5.00 g, 29.38 mmol) in DMF (80 mL) were added 1 , 1 ,3,3-tetramethoxypropane (14.50 mL, 88.15 mmol) and AcOH (0.34 mL, 5.88 mmol). The reaction mixture was stirred at 100 °C for 14 h, and then concentrated in vacuo. The residue was partitioned between DCM (50 mL) and water (50 mL). The organic phase was separated and the aqueous phase was extracted with DCM (100 mL x 3). The combined organic phases were washed with brine (100 mL), dried over anhydrous Na₂S04, filtered and concentrated in vacuo. The residue was purified by a silica gel column chromatography (a solution of NH₃in MeOH (7 M)/DCM (v/v) =1/100) to give the title compound as a pale yellow solid (3.52 g, 58.1percent).MS (ESI, pos. ion) m/z: 207.1 [M+H]⁺;H NMR (400 MHz, CDC1 ): δ (ppm) 8.60 (dd, J= 4.40 Hz, 1.76 Hz, 1H), 8.46 (dd, J = 6.76 Hz, 1.76 Hz, 1H), 6.86 (dd, J = 6.72 Hz, 4.40 Hz, 1H), 4.50 (q, J = 7.08 Hz, 2H), 1.47 (t, J = 7.08 Hz, 3H).
58.1%	With acetic acid In N,N-dimethyl-formamide at 100℃; for 14 h;	To a solution of ethyl 3,5-diamino-1 -hydro-pyrazole-4-carboxylate (5.00 g, 29.38 mmol)In N, N-dimethylformamide ((80 mL)1,1,3,3-tetramethoxypropane (14.50 mL, 88.15 mmol)And acetic acid (0.34 mL, 5.88 mmol).After the reaction mixture was stirred at 100 ° C for 14 hours,Concentrate under reduced pressure. The resulting residue was dispersed in a mixed system of dichloromethane (50 mL) and water (50 mL), the organic phase was separated and the aqueous phase was extracted with dichloromethane (100 mL x 3). The combined organic phases were washed with saturated brine (100 mL x 3), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (NH3 in methanol (7M) / methylene chloride (v / v) = 1/100) to give the title compound as a pale yellow solid (3.52 g, 58.1percent).
35.3%	With triethylamine In N,N-dimethyl-formamide at 100℃; for 14 h;	ethyl 2-aminopyrazolo[l ,5-a]pyrimidine-3-carboxylateA mixture of ethyl 3,5-diamino-l H-pyrazole-4-carboxylate (1.0 g, 5.9 mmol), 1,1,3,3- tetramethoxypropane (2.9 mL, 18 mmol), triethylamine (2 mL, 10 mmol), and DMF (15 mL) was heated at 100 ⁰C for 14 hrs, then a further 2 mL of 1,1,3,3-tetramethoxypropane was added. After adding the additional 1,1,3,3-tetramethoxypropane, a significant by-product was noted and heating was stopped immediately. The reaction was cooled to room temperature and the DMF was removed in vacuo. The residue was partitioned between DCM and water, then the organic layer was concentrated and the residue purified by silica chromatography, eluting with 95:5 DCM: 2M methanolic ammonia solution to afford 420 mg (35percent) of ethyl 2-aminopyrazolo[l,5- a]pyrimidine-3-carboxylate. ¹H NMR (500 MHz, CDCl₃) δ 8.57 (dd, J = 4.3, 1.6, IH), 8.43 (dd, J = 6.7, 1.6, IH), 6.84 (dd, J = 6.7, 4.4, IH), 5.52 (s, 2H), 4.48 (q, J= 7.1, 2H), 1.45 (t, J= 7.1, 3H).

Reference： [1] Patent: WO2015/73267, 2015, A1, . Location in patent: Paragraph 318
[2] Patent: CN104650092, 2017, B, . Location in patent: Paragraph 0463-0464; 0473-0474
[3] Patent: WO2011/3065, 2011, A2, . Location in patent: Page/Page column 110-111
[4] Patent: US2015/336962, 2015, A1, . Location in patent: Paragraph 0478
[5] Patent: WO2017/48702, 2017, A1, . Location in patent: Paragraph 001169; 001170; 001172

[ 6825-71-4 ] Synthesis Path-Downstream 1~87

1
[ 4362-40-7 ]
[ 6825-71-4 ]
[ 108212-11-9 ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1986,vol. 51,p. 1512 - 1531

2
[ 141-97-9 ]
[ 6825-71-4 ]
2-amino-3-ethoxycarbonyl-5-methyl-7-hydroxypyrazolo<1,5-a>pyrimidine [ No CAS ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1982,vol. 18,p. 934 - 938
Zhurnal Organicheskoi Khimii,1982,vol. 18,p. 1079 - 1084
[2]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1995,vol. 34,p. 514 - 520

3
[ 141-97-9 ]
[ 6825-71-4 ]
2-Amino-3-ethoxycarbonyl-4,5-dihydro-7-methyl-5-oxo-pyrazolo<1,5-a>pyrimidine [ No CAS ]

Reference： [1]Archiv der Pharmazie,1983,vol. 316,p. 713 - 718

4
[ 141-97-9 ]
[ 6825-71-4 ]
7-Amino-4-methyl-pyrazolo[5,1-c][1,2,4]triazine-3,8-dicarboxylic acid diethyl ester [ No CAS ]

Reference： [1]Archiv der Pharmazie,1983,vol. 316,p. 713 - 718

5
[ 614-16-4 ]
[ 6825-71-4 ]
2,7-Diamino-5-phenyl-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid ethyl ester [ No CAS ]

Reference： [1]Archiv der Pharmazie,1987,vol. 320,p. 240 - 246

6
[ 614-16-4 ]
[ 6825-71-4 ]
7-Amino-3-cyano-4-phenyl-pyrazolo[5,1-c][1,2,4]triazine-8-carboxylic acid ethyl ester [ No CAS ]

Reference： [1]Archiv der Pharmazie,1983,vol. 316,p. 713 - 718

7
[ 94-02-0 ]
[ 6825-71-4 ]
[ 82820-00-6 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1982,vol. 18,p. 934 - 938
Zhurnal Organicheskoi Khimii,1982,vol. 18,p. 1079 - 1084

8
[ 94-02-0 ]
[ 6825-71-4 ]
2-Amino-3-ethoxycarbonyl-4,5-dihydro-7-phenyl-5-oxopyrazolo<1,5-a>pyrimidine [ No CAS ]

Reference： [1]Archiv der Pharmazie,1983,vol. 316,p. 713 - 718

9
[ 838-57-3 ]
[ 6825-71-4 ]
[ 82820-01-7 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1982,vol. 18,p. 934 - 938
Zhurnal Organicheskoi Khimii,1982,vol. 18,p. 1079 - 1084

10
[ 32061-16-8 ]
[ 6825-71-4 ]
[ 108194-84-9 ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1986,vol. 51,p. 1512 - 1531

11
[ 20413-05-2 ]
[ 6825-71-4 ]
2,7-Diamino-6-benzoyl-5-phenyl-4,5-dihydro-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid ethyl ester [ No CAS ]

Reference： [1]Archiv der Pharmazie,1987,vol. 320,p. 240 - 246

12
[ 79-37-8 ]
[ 6825-71-4 ]
[ 91173-73-8 ]
[ 91173-77-2 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1984,vol. 20,p. 782 - 785
Zhurnal Organicheskoi Khimii,1984,vol. 20,p. 860 - 863

13
[ 49765-05-1 ]
[ 6825-71-4 ]
2,5-Diamino-3-ethoxycarbonyl-6-cyano-4,7-dihydro-7-oxopyrazolo<1,5-a>pyrimidine [ No CAS ]

Reference： [1]Archiv der Pharmazie,1983,vol. 316,p. 713 - 718

14
[ 2700-22-3 ]
[ 6825-71-4 ]
2,7-Diamino-6-cyano-5-phenyl-4,5-dihydro-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid ethyl ester [ No CAS ]

Reference： [1]Archiv der Pharmazie,1987,vol. 320,p. 240 - 246

15
[ 6825-71-4 ]
[ 1572-57-2 ]
2,5,7-Triamino-6-cyano-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid ethyl ester [ No CAS ]

Reference： [1]Archiv der Pharmazie,1987,vol. 320,p. 240 - 246

16
[ 6825-71-4 ]
[ 124-40-3 ]
3,5-bis(3,3-dimethyl-1-triazeno)-4-ethoxycarbonyl-pyrazole [ No CAS ]

Reference： [1]Arzneimittel-Forschung/Drug Research,1984,vol. 34,p. 661 - 663

17
[ 6825-71-4 ]
[ 109-89-7 ]
3,5-bis-(3,3-diethyl-1-triazeno)-4-ethoxycarbonylpyrazole [ No CAS ]

Reference： [1]Arzneimittel-Forschung/Drug Research,1984,vol. 34,p. 661 - 663

18
[ 6825-71-4 ]
[ 107-13-1 ]
2,7-Diamino-3-ethoxycarbonyl-4,5-dihydropyrazolo<1,5-a>pyrimidine [ No CAS ]

Reference： [1]Archiv der Pharmazie,1983,vol. 316,p. 713 - 718

19
[ 6825-71-4 ]
[ 107-13-1 ]
7-Amino-3-cyano-3,4-dihydro-pyrazolo[5,1-c][1,2,4]triazine-8-carboxylic acid ethyl ester [ No CAS ]

Reference： [1]Archiv der Pharmazie,1983,vol. 316,p. 713 - 718

20
[ 6825-71-4 ]
[ 105-56-6 ]
[ 82819-90-7 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1982,vol. 18,p. 934 - 938
Zhurnal Organicheskoi Khimii,1982,vol. 18,p. 1079 - 1084

21
[ 6825-71-4 ]
[ 105-56-6 ]
2,7-Diamino-5-oxo-4,5-dihydro-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid ethyl ester [ No CAS ]

Reference： [1]Archiv der Pharmazie,1987,vol. 320,p. 240 - 246

22
[ 6825-71-4 ]
[ 105-56-6 ]
3-Amino-5-{N'-[1-cyano-1-ethoxycarbonyl-meth-(Z)-ylidene]-hydrazino}-1H-pyrazole-4-carboxylic acid ethyl ester [ No CAS ]

Reference： [1]Archiv der Pharmazie,1983,vol. 316,p. 713 - 718

23
[ 6825-71-4 ]
[ 108-26-9 ]
3-Amino-5-(5-hydroxy-3-methyl-1H-pyrazol-4-ylazo)-1H-pyrazole-4-carboxylic acid ethyl ester [ No CAS ]

Reference： [1]Archiv der Pharmazie,1987,vol. 320,p. 240 - 246

24
[ 6825-71-4 ]
[ 89-25-8 ]
3-Amino-5-(5-hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-ylazo)-1H-pyrazole-4-carboxylic acid ethyl ester [ No CAS ]

Reference： [1]Archiv der Pharmazie,1987,vol. 320,p. 240 - 246

25
[ 6825-71-4 ]
[ 999-97-3 ]
[ 108183-26-2 ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1986,vol. 51,p. 1512 - 1531

26
[ 6825-71-4 ]
[ 2216-94-6 ]
[ 82819-95-2 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1982,vol. 18,p. 934 - 938
Zhurnal Organicheskoi Khimii,1982,vol. 18,p. 1079 - 1084

27
[ 6825-71-4 ]
[ 18440-58-9 ]
6-Amino-7-ethoxycarbonyl-3-methyl-2-phenylazoimidazopyrazole [ No CAS ]

Reference： [1]Archiv der Pharmazie,1987,vol. 320,p. 240 - 246

28
[ 6825-71-4 ]
[ 123-54-6 ]
2-Amino-3-ethoxycarbonyl-5,7-dimethylpyrazolo<1,5-a>pyrimidine [ No CAS ]

Reference： [1]Archiv der Pharmazie,1983,vol. 316,p. 713 - 718
[2]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1995,vol. 34,p. 514 - 520

29
[ 6825-71-4 ]
[ 135-19-3 ]
2-Amino-1,4,5,11c-tetraaza-cyclopenta[c]phenanthrene-3-carboxylic acid ethyl ester [ No CAS ]

Reference： [1]Archiv der Pharmazie,1983,vol. 316,p. 713 - 718

30
[ 6825-71-4 ]
[ 637-44-5 ]
[ 82819-89-4 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1982,vol. 18,p. 934 - 938
Zhurnal Organicheskoi Khimii,1982,vol. 18,p. 1079 - 1084

31
[ 6825-71-4 ]
[ 109-77-3 ]
(3-Amino-4-oxo-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-yl)-acetonitrile [ No CAS ]

Reference： [1]Archiv der Pharmazie,1987,vol. 320,p. 240 - 246

32
[ 6825-71-4 ]
[ 109-77-3 ]
3-Amino-5-(N'-dicyanomethylene-hydrazino)-1H-pyrazole-4-carboxylic acid ethyl ester [ No CAS ]

Reference： [1]Archiv der Pharmazie,1983,vol. 316,p. 713 - 718

33
[ 6825-71-4 ]
[ 140-88-5 ]
[ 82819-92-9 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1982,vol. 18,p. 934 - 938
Zhurnal Organicheskoi Khimii,1982,vol. 18,p. 1079 - 1084

34
[ 6825-71-4 ]
[ 140-88-5 ]
2-Amino-3-etoxycarbonyl-4,5,6,7-tetrahydro-7-oxo-pyrazolo<1,5-a>pyrimidine [ No CAS ]

Reference： [1]Archiv der Pharmazie,1987,vol. 320,p. 240 - 246

35
[ 6825-71-4 ]
[ 74440-34-9 ]

Reference： [1]Zeitschrift fur Chemie,1980,vol. 20,p. 95 - 96

36
[ 6825-71-4 ]
[ 74440-35-0 ]

Reference： [1]Zeitschrift fur Chemie,1980,vol. 20,p. 95 - 96

37
[ 611-10-9 ]
[ 6825-71-4 ]
2-amino-3-carbethoxy-6,7-dihydro-8-hydroxy-5H-cyclopenta<d>pyrazolo<1,5-a>pyrimidine [ No CAS ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1995,vol. 34,p. 514 - 520

38
[ 609-14-3 ]
[ 6825-71-4 ]
2-Amino-7-hydroxy-5,6-dimethyl-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid ethyl ester [ No CAS ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1995,vol. 34,p. 514 - 520

39
[ 5147-80-8 ]
[ 6825-71-4 ]
3-carbethoxy-6-cyano-2,7-diamino-5-methylthiopyrazolo<1,5-a>pyrimidine [ No CAS ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1995,vol. 34,p. 514 - 520

40
[ 51507-10-9 ]
[ 6825-71-4 ]
2-Amino-9-methoxy-5-methylsulfanyl-6,7-dihydro-1,4,11c-triaza-cyclopenta[c]phenanthrene-3-carboxylic acid ethyl ester [ No CAS ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1995,vol. 34,p. 514 - 520

41
[ 6825-71-4 ]
[ 120-46-7 ]
2-amino-3-carbethoxy-5,7-diphenylpyrazolo<1,5-a>pyrimidine [ No CAS ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1995,vol. 34,p. 514 - 520

42
[ 6825-71-4 ]
[ 1655-07-8 ]
2-amino-3-carbethoxy-9-hydroxy-5,6,7,8-tetrahydropyrazolo<5,1-b>quinazoline [ No CAS ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1995,vol. 34,p. 514 - 520

43
[ 6825-71-4 ]
[ 105-50-0 ]
2-amino-3-carbethoxy-5-carbethoxymethyl-7-hydroxypyrazolo<1,5-a>pyrimidine [ No CAS ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1995,vol. 34,p. 514 - 520

44
[ 6825-71-4 ]
[ 609-15-4 ]
2-Amino-6-chloro-7-hydroxy-5-methyl-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid ethyl ester [ No CAS ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1995,vol. 34,p. 514 - 520

45
[ 6825-71-4 ]
[ 94-05-3 ]
2,7-Diamino-pyrazolo[1,5-a]pyrimidine-3,6-dicarboxylic acid diethyl ester [ No CAS ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1995,vol. 34,p. 514 - 520

46
[ 6825-71-4 ]
[ 87-13-8 ]
2-Amino-7-hydroxy-pyrazolo[1,5-a]pyrimidine-3,6-dicarboxylic acid diethyl ester [ No CAS ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1995,vol. 34,p. 514 - 520

47
[ 6825-71-4 ]
[ 82819-95-2 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1982,vol. 18,p. 934 - 938
Zhurnal Organicheskoi Khimii,1982,vol. 18,p. 1079 - 1084

48
[ 6825-71-4 ]
[ 91173-73-8 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1984,vol. 20,p. 782 - 785
Zhurnal Organicheskoi Khimii,1984,vol. 20,p. 860 - 863

49
[ 6825-71-4 ]
N,N'-bis(3-amino-4-ethoxycarbonyl-5-pyrazolyl)oxamide [ No CAS ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1984,vol. 20,p. 782 - 785
Zhurnal Organicheskoi Khimii,1984,vol. 20,p. 860 - 863

50
[ 6825-71-4 ]
7-Amino-3-cyano-4-hydroxy-pyrazolo[5,1-c][1,2,4]triazine-8-carboxylic acid ethyl ester [ No CAS ]

Reference： [1]Archiv der Pharmazie,1983,vol. 316,p. 713 - 718

51
[ 6825-71-4 ]
[ 108183-30-8 ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1986,vol. 51,p. 1512 - 1531

52
[ 102-52-3 ]
[ 6825-71-4 ]
[ 1260169-02-5 ]

Yield	Reaction Conditions	Operation in experiment
58.1%	With acetic acid; at 100℃; for 14.0h;	To a solution of ethyl 3,5-diamino-lH-pyrazole-4-carboxylate (5.00 g, 29.38 mmol) in DMF (80 mL) were added 1 , 1 ,3,3-tetramethoxypropane (14.50 mL, 88.15 mmol) and AcOH (0.34 mL, 5.88 mmol). The reaction mixture was stirred at 100 C for 14 h, and then concentrated in vacuo. The residue was partitioned between DCM (50 mL) and water (50 mL). The organic phase was separated and the aqueous phase was extracted with DCM (100 mL x 3). The combined organic phases were washed with brine (100 mL), dried over anhydrous Na2S04, filtered and concentrated in vacuo. The residue was purified by a silica gel column chromatography (a solution of NH3in MeOH (7 M)/DCM (v/v) =1/100) to give the title compound as a pale yellow solid (3.52 g, 58.1%).MS (ESI, pos. ion) m/z: 207.1 [M+H]+; H NMR (400 MHz, CDC1 ): delta (ppm) 8.60 (dd, J= 4.40 Hz, 1.76 Hz, 1H), 8.46 (dd, J = 6.76 Hz, 1.76 Hz, 1H), 6.86 (dd, J = 6.72 Hz, 4.40 Hz, 1H), 4.50 (q, J = 7.08 Hz, 2H), 1.47 (t, J = 7.08 Hz, 3H).
58.1%	With acetic acid; In N,N-dimethyl-formamide; at 100℃; for 14.0h;	To a solution of ethyl 3,5-diamino-1 -hydro-pyrazole-4-carboxylate (5.00 g, 29.38 mmol)In N, N-dimethylformamide ((80 mL)1,1,3,3-tetramethoxypropane (14.50 mL, 88.15 mmol)And acetic acid (0.34 mL, 5.88 mmol).After the reaction mixture was stirred at 100 C for 14 hours,Concentrate under reduced pressure. The resulting residue was dispersed in a mixed system of dichloromethane (50 mL) and water (50 mL), the organic phase was separated and the aqueous phase was extracted with dichloromethane (100 mL x 3). The combined organic phases were washed with saturated brine (100 mL x 3), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (NH3 in methanol (7M) / methylene chloride (v / v) = 1/100) to give the title compound as a pale yellow solid (3.52 g, 58.1%).
35.3%	With triethylamine; In N,N-dimethyl-formamide; at 100℃; for 14.0h;	ethyl 2-aminopyrazolo[l ,5-a]pyrimidine-3-carboxylateA mixture of ethyl 3,5-diamino-l H-pyrazole-4-carboxylate (1.0 g, 5.9 mmol), 1,1,3,3- tetramethoxypropane (2.9 mL, 18 mmol), triethylamine (2 mL, 10 mmol), and DMF (15 mL) was heated at 100 0C for 14 hrs, then a further 2 mL of 1,1,3,3-tetramethoxypropane was added. After adding the additional 1,1,3,3-tetramethoxypropane, a significant by-product was noted and heating was stopped immediately. The reaction was cooled to room temperature and the DMF was removed in vacuo. The residue was partitioned between DCM and water, then the organic layer was concentrated and the residue purified by silica chromatography, eluting with 95:5 DCM: 2M methanolic ammonia solution to afford 420 mg (35%) of ethyl 2-aminopyrazolo[l,5- a]pyrimidine-3-carboxylate. 1H NMR (500 MHz, CDCl3) delta 8.57 (dd, J = 4.3, 1.6, IH), 8.43 (dd, J = 6.7, 1.6, IH), 6.84 (dd, J = 6.7, 4.4, IH), 5.52 (s, 2H), 4.48 (q, J= 7.1, 2H), 1.45 (t, J= 7.1, 3H).

With acetic acid; at 25 - 95℃;

Another exemplary study was carried out as follow: Compound J and AcOH (7.5 volumes) were charged to an appropriately sized jacketed reactor. Mixing was started and the jacket was set to maintain an internal temperature of 25 C . Tetramethoxypropane (1.01 equivalents) was charged to the reactor and the j acket was set to maintain an internal temperature of 95 C. Once at temperature, the reaction continued mixing for 1.5 hours and then an IPC sample was taken. The passing criteria for this IPC was 60 C to prevent premature precipitation. Once the target volume was reached the jacket was set to maintain an internal temperature of 50 C. A 4 M solution of NaOH was then charged to the reactor via cannula to neutralize the remaining AcOH. This typically required approximately 10 volumes of the base solution. The neutralization was monitored by pH probe. Solids began to precipitate during the course of the charge. Once neutralized, the slurry was cooled to 20 C and held at that temperature for 1 hour prior to isolation via Buchner funnel. The cake was washed twice with 2 volumes of water and once with 2 volumes of MeOH. The solids were then dried to constant weight in a vacuum oven to provide Compound H. This procedure had been performed on 110 g scale to produce a granular light brown solid.

Reference： [1]Patent: WO2015/73267,2015,A1 .Location in patent: Paragraph 318
[2]Patent: CN104650092,2017,B .Location in patent: Paragraph 0463-0464; 0473-0474
[3]Patent: WO2011/3065,2011,A2 .Location in patent: Page/Page column 110-111
[4]Patent: US2015/336962,2015,A1 .Location in patent: Paragraph 0478
[5]Patent: WO2017/48702,2017,A1 .Location in patent: Paragraph 001169; 001170; 001172

53
[ 105-56-6 ]
[ 6825-71-4 ]

Reference： [1]Patent: WO2011/3065,2011,A2
[2]Patent: WO2015/73267,2015,A1
[3]Patent: US2015/336962,2015,A1
[4]Patent: WO2017/48702,2017,A1
[5]Patent: CN104650092,2017,B
[6]Patent: CN108003161,2018,A
[7]Patent: WO2019/23417,2019,A1
[8]Patent: EP3533796,2019,A1
[9]Patent: EP3674307,2020,A1

54
[ 49765-05-1 ]
[ 6825-71-4 ]

Yield	Reaction Conditions	Operation in experiment
74.2%	With hydrazine; In water; N,N-dimethyl-formamide; at 100℃; for 2h;	To a solution of (Z)-ethyl 3-amino-4,4,4-trichloro-2-cyanobut-2-enoate (82.34 g, 319.77 mmol) in DMF (250 mL) was added a solution of hydrazine in water (50% [w/w], 46.08 g, 718.88 mmol). The reaction mixture was stirred at 100 C for 2 h and concentrated in vacuo. The residue was diluted with DCM (100 mL), and the resulting mixture was stood overnight. The solid was collected by Alteration, and then washed with DCM (50 mL x 3) to give the title compound as a pale yellow solid (40.40 g, 74.2%).MS (ESI, pos. ion) m/z: 171.0 [M+H]+;lH NMR (400 MHz, OMSO-ds): delta (ppm) 5.35 (s, 4H), 4.14 (q, J = 7.12 Hz, 2H), 1.24 (t, J =7.12 Hz, 3H).
74.2%	With hydrazine hydrate; In N,N-dimethyl-formamide; at 100℃; for 2h;	To a solution of ethyl (Z) -3-amino-4,4,4-trichloro-2-cyano-2-enebutyrate (82.34 g, 319.77 mmol)In N, N-dimethylformamide (250 mL)Aqueous solution of hydrazine hydrate (50% [w / w], 46.08 g, 718.88 mmol) was added to the solution,After the resultant reaction solution was stirred at 100 C for 2 hours,Concentrate under reduced pressure. The resulting residue was diluted with dichloromethane (100 mL) and the resulting mixture was allowed to stand overnight. Filtration, collection of the solid and washing with dichloromethane (50 mL x 3) yielded the title compound as a pale yellow solid (40.40 g, 74.2%).
67%	With hydrazine hydrate; In N,N-dimethyl-formamide; at 100℃; for 1.5h;	Ethyl (Z)-3-amino-4,4,4-trichloro-2-cyano-crotonate (92.1 g)Slow in DMF solution (250mL)Slowly add hydration hydrazine (50g),The reaction mixture was heated to 100C and stirred for 1.5 hours.Concentrate to remove the solvent,The residue is slurried with dichloromethane.Then let it stand overnight.Collect the solid by suction,Dichloromethane elution,dry,The title compound was obtained (41.0 g, 67% yield).

58%	With hydrazine; In N,N-dimethyl-formamide; at 100℃; for 1h;	ethyl 3 ,5-diamino- 1 H-pyrazole-4-carboxylateHydrazine (2.19 mL, 70 mmol) was added to (Z)-ethyl 3-amino-4,4,4-trichloro-2-cyanobut-2- enoate (15.0 g, 58 mmol) in DMF (50 mL). The reaction mixture was heated to 100 0C for 1 hr, then cooled to room temperature. The DMF was removed in vacuo, then the residue was slurried in a 95:5 mixture of DCM: 2M methanolic ammonia solution. The resulting precipitate was filtered off, washed with a 95:5 mixture of DCM:MeOH, and dried under vacuum to afford 5.72g (58%) of ethyl 3,5-diamino-lH-pyrazole-4-carboxylate as a white solid. 1H NMR (400 MHz, DMSO) delta 10.53 (s, IH), 5.28 (br, 4H), 4.14 (q, /= 7.1, 2H), 1.33 - 1.15 (t, J = 7.1, 3H).
41 g	With hydrazine hydrate; In N,N-dimethyl-formamide; at 100℃; for 1.5h;	To a solution of ethyl (Z)-3-amino-4,4,4-trichloro-2-cyano-butenoate (92.1 g) in DMF (250 mL) was slowly added hydrazine hydrate (50 g) dropwise, and the reaction mixture was heated to 100C and reacted for 1.5 hours under stirring. The solvent was removed by concentration, and the residue was slurried with dichloromethane and then allowed to stand overnight. The resulting mixture was suction-filtered, and the solid was collected, rinsed with dichloromethane and dried to afford the title compound (41.0 g). 1H NMR (400 MHz, DMSO-d6) delta 10.4 (brs, 1H), 5.35 (brs, 4H), 4.13 (q, J = 7.2 Hz, 2H), 1.24 (t, J = 7.2 Hz, 3H). m/z=171[M+1]+.
	With hydrazine hydrate;	Step B-10: Synthesis of ethyl 3,5-diamino-1H-pyrazole-4-carboxylate To a solution of ethyl (Z)-3-amino-4,4,4-trichloro-2-cyano-butenoate (92.1 g) in DMF (250 mL) was slowly added hydrazine hydrate (50 g, a concentration of 80%) dropwise. The reaction mixture was heated to 100 C and stirred for 1.5 hours, and then concentrated to remove the solvent. The residue was slurried with dichloromethane, and then suction-filtered. The solid was washed with dichloromethane and dried to afford the title compound (41.0 g). 1H NMR (400 MHz, DMSO-d6)delta10.4 (brs, 1H), 5.35 (brs, 4H), 4.13 (q, J = 7.2 Hz, 2H), 1.24 (t, J = 7.2 Hz, 3H).

Reference： [1]Patent: WO2015/73267,2015,A1 .Location in patent: Paragraph 317; 367
[2]Patent: CN104650092,2017,B .Location in patent: Paragraph 0463-0464; 0469-0470
[3]Patent: CN108003161,2018,A .Location in patent: Paragraph 0849; 0855-0857
[4]Patent: WO2011/3065,2011,A2 .Location in patent: Page/Page column 110
[5]Patent: EP3533796,2019,A1 .Location in patent: Paragraph 0113; 0116; 0117
[6]Patent: EP3674307,2020,A1 .Location in patent: Paragraph 0118; 0120

55
[ 6825-71-4 ]
[ 1260169-03-6 ]

Reference： [1]Patent: WO2011/3065,2011,A2
[2]Patent: US2015/336962,2015,A1

56
[ 504-02-9 ]
[ 4637-24-5 ]
[ 6825-71-4 ]
[ 1372858-94-0 ]

Reference： [1]Beilstein Journal of Organic Chemistry,2012,vol. 8,p. 18 - 24

57
[ 6825-71-4 ]
C₁₆H₁₈N₄O₄S [ No CAS ]

Reference： [1]Patent: US2013/267521,2013,A1

58
[ 5436-21-5 ]
[ 6825-71-4 ]
[ 1466565-68-3 ]

Yield	Reaction Conditions	Operation in experiment
		Example 123 Compound 142 was prepared in 3 steps from <strong>[6825-71-4]ethyl 3,5-diamino-1H-pyrazole-4-carboxylate</strong> in the following manner: Ethyl 3,5-diamino-1H-pyrazole-4-carboxylate (1.0 eq, 2.8 mmol) was dissolved in 6 mL N,N-dimethylformamide. 4,4-Dimethyoxy-2-butanone (2.0 eq) was added and the reaction was heated to 110 C. for 1 h, after which acetic acid (1.0 eq) was added and the reaction was heated for an additional 2 h. The mixture was allowed to cool and was neutralized with saturated sodium bicarbonate, transferred to a separatory funnel and extracted with 1* ethyl acetate and 2* methylene chloride. The organic layers were combined, dried over MgSO4 and concentrated until there was <20 mL of solvent remaining. Excess hexanes were added until a solid crashed out. The resulting solid was collected via vacuum filtration to provide the desired pyrazolopyrimidine. This solid (0.59 mmol, 1.0 eq) was then dissolved in ethanol/water (10 mL, 1:1 v/v).

Reference： [1]Patent: US2013/267521,2013,A1 .Location in patent: Paragraph 0906

59
[ 6825-71-4 ]
[ 123-54-6 ]
[ 1466565-69-4 ]

Yield	Reaction Conditions	Operation in experiment
		Compound 151 was prepared in 3 steps from <strong>[6825-71-4]ethyl 3,5-diamino-1H-pyrazole-4-carboxylate</strong> in the following manner: Ethyl 3,5-diamino-1H-pyrazole-4-carboxylate (1.0 eq, 5.7 mmol) was dissolved in 6 mL N,N-dimethylformamide. Pentane-2,4-dione (2.0 equiv) and acetic acid (5.0 equiv) were added and the reaction was heated to 110 C. for 2 h, after which there was no more starting material by TLC analysis. The mixture was allowed to cool and was neutralized with saturated sodium bicarbonate. The resulting solid was collected via vacuum filtration to provide the desired pyrazolopyrimidine. This solid (4.7 mmol, 1.0 eq) was then dissolved in ethanol/water (10 mL, 1:1 v/v). Lithium hydroxide (30 equiv) was then added and the reaction was heated to 70 C. for 2 h. The reaction was allowed to cool, after which 3 N HCl was added dropwise until the mixture had a pH<2. The resulting solid was collected via vacuum filtration and washed with excess water to provide Compound 151

Reference： [1]Patent: US2013/267521,2013,A1 .Location in patent: Paragraph 0918

60
[ 1001-26-9 ]
[ 6825-71-4 ]
[ 1466565-59-2 ]

Yield	Reaction Conditions	Operation in experiment
		Ethyl 3,5-diamino-1H-pyrazole-4-carboxylate (9.2 mmol, 1.0 eq) was dissolved in N,N-dimethyl formamide (20 mL) and cesium carbonate (1.5 eq), and <strong>[1001-26-9]ethyl 3-ethoxyacrylate</strong> (1.5 eq) were added. The reaction was heated to 110° C. for 16 h. The mixture was cooled. Acetic acid (1.2 mL) was added, followed by 90 mL of water. The mixture was stirred until a solid formed, which was collected by filtration, and washed with excess water to provide compound 124.

Reference： [1]Patent: US2013/267521,2013,A1 .Location in patent: Paragraph 0882

61
[ 66480-84-0 ]
[ 6825-71-4 ]
[ 1466565-71-8 ]
[ 1466565-72-9 ]

Yield	Reaction Conditions	Operation in experiment
		Compound 175 was prepared in 3 steps from <strong>[6825-71-4]ethyl 3,5-diamino-1H-pyrazole-4-carboxylate</strong> in the following manner: A mixture of <strong>[6825-71-4]ethyl 3,5-diamino-1H-pyrazole-4-carboxylate</strong> (1.5 mmol, 1.0 equiv) and 1,1-dimethoxy-4-methylpentan-3-one (2.0 equiv) in DMF (4 mL) under an Argon atmosphere was stirred for 5 min at room temperature before heating at 110 C. for 1 h. After 1 h, acetic acid (1.0 equiv) was added and an additional 1.0 equiv was added after 2.5 h. The reaction was stirred and heated for 72 h after which 30 mL saturated sodium bicarbonate was added and the mixture was filtrated. The aqueous layer was extracted with 40 mL methylene chloride. The organic layers were combined, washed with brine (2×30 mL), dried over magnesium sulfate and concentrated to a crude mixture of 173 and 174 which was used directly in the next step.

Reference： [1]Patent: US2013/267521,2013,A1 .Location in patent: Paragraph 0935

62
[ 2802-08-6 ]
[ 6825-71-4 ]
C₁₀H₁₂N₄O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With acetic acid; at 110℃;Sealed tube;	[00776] Ethyl 3,5-diamino-1H-pyrazole-4-carboxylate (1 g, 5.88 mmol) was dissolved in 25 mL acetic acid. <strong>[2802-08-6](E)-4-(dimethylamino)but-3-en-2-one</strong> (698 mg, 6.2 mmol) was added and the reaction was heated in a sealed tube at 110C. The reaction is heated for 30h after which point the mixture was neutralized with saturated sodium bicarbonate and extracted with one portion of EtOAc and one portion of DCM. The organic layers were combined, dried over MgSO4 and concentrated until there was < 20 mL of solvent left. Hexane was added and the resulting solid was isolated via vacuum filtration. The residue was purified by flash chromatography (12g using 0 to 60% EtOAc/DCM) to give the ester. The ester (178 mg, 0.808 mmol) was suspended in 8 mL EtOH/water (1:1). LiOH 2M (4041 jil, 8.08 mmol) was added and the reaction was heated to 70C. After 2 h, EtOH was removed and the pH was brought to 2 by addition of 2 M HC1. The solids were filtered and wash with water to provide 2-amino-7- methylpyrazolo[ 1 ,5-a]pyrimidine-3-carboxylic acid ([M+H] = 193.2).

Reference： [1]Patent: WO2015/51241,2015,A1 .Location in patent: Paragraph 00776

63
[ 6825-71-4 ]
2-amino-5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylic acid ethyl ester [ No CAS ]

Reference： [1]Patent: WO2015/73267,2015,A1
[2]Patent: WO2019/23417,2019,A1
[3]Patent: EP3533796,2019,A1
[4]Patent: EP3674307,2020,A1

64
[ 6825-71-4 ]
ethyl 2-(bis(tert-butoxycarbonyl)amino)-5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylate [ No CAS ]

Reference： [1]Patent: WO2015/73267,2015,A1
[2]Patent: CN104650092,2017,B

65
[ 6825-71-4 ]
2-((tert-butoxycarbonyl)amino)pyrazolo[1,5-a]pyrimidine-3-formic acid ethyl ester [ No CAS ]

Reference： [1]Patent: WO2015/73267,2015,A1
[2]Patent: CN104650092,2017,B

66
[ 6825-71-4 ]
2-amino-5-bromopyrazolo[1,5-a]pyrimidine-3-carboxylic acid ethyl ester [ No CAS ]

Reference： [1]Patent: WO2015/73267,2015,A1

67
[ 6825-71-4 ]
2-(bis(tert-butyloxycarbonyl)amino)-5-bromo-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid ethyl ester [ No CAS ]

Reference： [1]Patent: WO2015/73267,2015,A1
[2]Patent: CN104650092,2017,B

68
[ 6825-71-4 ]
ethyl 2-(bis(tert-butoxycarbonyl)amino)-5-cyclopropylpyrazolo[1,5-a]pyrimidine-3-carboxylate [ No CAS ]

Reference： [1]Patent: WO2015/73267,2015,A1
[2]Patent: CN104650092,2017,B

69
[ 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

70
[ 22071-00-7 ]
[ 6825-71-4 ]

Yield	Reaction Conditions	Operation in experiment
81.7%	With hydrazine hydrate; In N,N-dimethyl-formamide; at 100℃; for 2h;	To a solution of ethyl A-3-2 (100 g, 388 mmol, 1.00 eq. ) in DMF (500 mL) was added hydrazine hydrate (311 g, 3.11 mol, 50.0% purity, 8.00 eq. ). The mixture was stirred at 100 C for 2 hours. Removed the solvent and added DCM (500 mL), the resulting mixture was stirred for 12 hours. The solid was filtered and washed with DCM (200 mL) to give A-3-3 (60.0 g, 317 mmol, yield = 81.7%) as brown solid. 1H NMR (400 MHz, DMSO-d6) delta = 7.91 (s, IH), 7.50 (s, 2H), 4.57 (s, 2H), 4.03 (q, 7=7.2 Hz, 2H), 1.16 (t, 7=7.2 Hz, 3H).

Reference： [1]Patent: WO2019/23417,2019,A1 .Location in patent: Paragraph 0250; 0252
[2]Patent: US2015/336962,2015,A1 .Location in patent: Paragraph 0478

71
[ 121020-70-0 ]
[ 6825-71-4 ]

Reference： [1]Patent: WO2017/48702,2017,A1

72
C₈H₁₂N₂O₄ [ No CAS ]
[ 6825-71-4 ]

Reference： [1]Patent: WO2017/48702,2017,A1

73
β-Cyano-β-ethoxycarbonyl-α-amino-α-hydrazinoethylen [ No CAS ]
[ 6825-71-4 ]

Yield	Reaction Conditions	Operation in experiment
	In butan-1-ol; at 105 - 110℃;	Compound M and 1-BuOH (6.5 volumes) were charged to an appropriately sized jacketed reactor. Mixing was started and the jacket was set to maintain an internal temperature of 25 C. Aqueous ammonia (1.1 equivalents) was charged to the reactor. There was an initial endotherm from the dissolution of the ammonia and then a very mild exotherm as the reaction begins. An IPC sample should be taken following a minimum of 1.5 hours and the passing criteria is < 1 area% remaining starting material. Once a passing IPC was obtained, hydrazine monohydrate (1.5 equivalents) was charged to the reactor and the jacket was set to maintain an internal temperature of 70 C. After 2 hours an IPC sample can be taken and a passing test has < 1 area% remaining intermediate (Compound L). Once this passing IPC occurred, the jacket was set to maintain an internal temperature of 105 - 110 C (reflux). The reaction was then allowed to proceed for about 40 hours.

Reference： [1]Patent: WO2017/48702,2017,A1 .Location in patent: Paragraph 001166; 001167

74
[ 6825-71-4 ]
C₁₄H₁₆⁽²⁾H₂N₄O₄ [ No CAS ]

Reference： [1]Patent: WO2017/161116,2017,A1

75
malonaldehyde-1,3-d2 bis(diethyl acetal) [ No CAS ]
[ 6825-71-4 ]
C₉H₈⁽²⁾H₂N₄O₂ [ No CAS ]

Reference： [1]Patent: WO2017/161116,2017,A1 .Location in patent: Paragraph 00432

76
[ 6825-71-4 ]
ethyl 2-(tert-butyloxycarbonylamino)-5-methoxypyrazolo[1,5-a]pyrimidine-3-carboxylate [ No CAS ]

Reference： [1]Patent: CN104650092,2017,B

77
[ 6825-71-4 ]
C₁₁H₈ClF₃N₄O₃ [ No CAS ]

Reference： [1]Patent: WO2019/23417,2019,A1

78
[ 6825-71-4 ]
ethyl 2-amino-5-((2-chloro-3-fluoro-6-hydroxybenzyl)(ethyl)amino)pyrazolo[1,5-a]pyrimidine-3-carboxylate [ No CAS ]

Reference： [1]Patent: WO2019/23417,2019,A1

79
[ 6825-71-4 ]
ethyl 2-amino-5-((2-bromo-3-fluoro-6-hydroxybenzyl)(ethyl)amino)pyrazolo[1,5-a]pyrimidine-3-carboxylate [ No CAS ]

Reference： [1]Patent: WO2019/23417,2019,A1

80
[ 6825-71-4 ]
C₂₆H₃₄ClFN₆O₅ [ No CAS ]

Reference： [1]Patent: WO2019/23417,2019,A1

81
[ 6825-71-4 ]
(R)-2-amino-5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid ethyl ester [ No CAS ]

Reference： [1]Patent: EP3533796,2019,A1

82
[ 6825-71-4 ]
2-amino-5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid ethyl ester [ No CAS ]

Reference： [1]Patent: EP3533796,2019,A1

83
[ 6825-71-4 ]
5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)-2-(((4-nitrophenoxy)carbonyl)amino)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid ethyl ester [ No CAS ]

Reference： [1]Patent: EP3533796,2019,A1

84
[ 6825-71-4 ]
ethyl 5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)-2-((4-methylphenyl)sulfonylamino)pyrazolo[1,5-a]pyrimidine-3-carboxylate [ No CAS ]

Reference： [1]Patent: EP3533796,2019,A1

85
[ 6825-71-4 ]
ethyl (R)-5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)-2-(methylamino)pyrazolo[1,5-a]pyrimidine-3-carboxylate [ No CAS ]

Reference： [1]Patent: EP3533796,2019,A1

86
[ 6825-71-4 ]
ethyl 2-amino-5-((2R,4S)-2-(2,5-difluorophenyl)-4-fluoropyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylate [ No CAS ]

Reference： [1]Patent: EP3533796,2019,A1

87
[ 6825-71-4 ]
5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)-2-(3-methylureido)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid ethyl ester [ No CAS ]

Reference： [1]Patent: EP3533796,2019,A1

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Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 6825-71-4 ] {[proInfo.proName]}

Quality Control of [ 6825-71-4 ]

Related Doc. of [ 6825-71-4 ]

Product Details of [ 6825-71-4 ]

Calculated chemistry of [ 6825-71-4 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 6825-71-4 ]

Application In Synthesis of [ 6825-71-4 ]

[ 6825-71-4 ] Synthesis Path-Upstream 1~5

[ 6825-71-4 ] Synthesis Path-Downstream 1~87

Related Functional Groups of [ 6825-71-4 ]

Esters

Amines

Related Parent Nucleus of [ 6825-71-4 ]

Pyrazoles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 6825-71-4 ]

Related Parent Nucleus of
[ 6825-71-4 ]