[ CAS No. 13223-25-1 ] {[proInfo.proName]}

Name: 13223-25-1|2-Chloro-4,6-dimethoxypyrimidine|95%
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Quality Control of [ 13223-25-1 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 13223-25-1 ]

Product Details of [ 13223-25-1 ]

CAS No. :	13223-25-1	MDL No. :	MFCD00274530
Formula :	C₆H₇ClN₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	PBEKEFWBLFBSGQ-UHFFFAOYSA-N
M.W :	174.59	Pubchem ID :	5152323
Synonyms :

Calculated chemistry of [ 13223-25-1 ] Expand+

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.33
Num. rotatable bonds :	2
Num. H-bond acceptors :	4.0
Num. H-bond donors :	0.0
Molar Refractivity :	40.03
TPSA :	44.24 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.11 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.2
Log Po/w (XLOGP3) :	1.77
Log Po/w (WLOGP) :	1.15
Log Po/w (MLOGP) :	0.1
Log Po/w (SILICOS-IT) :	1.5
Consensus Log Po/w :	1.34

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.31
Solubility :	0.857 mg/ml ; 0.00491 mol/l
Class :	Soluble
Log S (Ali) :	-2.32
Solubility :	0.841 mg/ml ; 0.00482 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.52
Solubility :	0.527 mg/ml ; 0.00302 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.96

Safety of [ 13223-25-1 ]

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

Application In Synthesis of [ 13223-25-1 ]

* 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 [ 13223-25-1 ]
Downstream synthetic route of [ 13223-25-1 ]

[ 13223-25-1 ] Synthesis Path-Upstream 1~4

1
[ 13223-25-1 ]
[ 128276-49-3 ]
[ 5270-94-0 ]

Reference： [1] Tetrahedron, 1999, vol. 55, # 2, p. 405 - 412

2
[ 36315-01-2 ]
[ 13223-25-1 ]

Yield	Reaction Conditions	Operation in experiment
29.9%	With hydrogenchloride; sodium hydroxide; sodium nitrite In water; ethyl acetate	REFERENTIAL EXAMPLE 1 Preparation of 2-chloro-4,6-dimethoxypyrimidine 1,260 ml of 36percent hydrochloric acid were charged in a 5-l four-necked flask and then cooled to 0° C. After 180 g (1.16 moles) of 2-amino-4,6-dimethoxypyrimidine were added in small portions into the flask, the resulting mixture was stirred for about 1 hour until the reaction mixture changed into a syrupy form. After the reaction mixture was cooled to -15° C., 260 ml of 159 g (2.3 moles) of NaNO₂ in H₂ O were added dropwise over about 1 hour under vigorous stirring. After completion of the dropwise addition, the resulting mixture was stirred at -15° to -10° C. for additional 1 hour so that the reaction was brought to completion. While the reaction mixture was retained at -5° C., 1.5 l of a 30percent aqueous solution of NaOH were charged dropwise so that the reaction mixture was neutralized to pH 7. By filtration under reduced pressure, a clay-like material of a purple color was collected. The target compound was extracted from the clay-like material using 3 l of ethyl acetate. Through the procedures of washing with water, drying over anhydrous sodium sulfate and removal of the solvent, 63 g of bluish crude crystals were obtained. They were crystallized further by silica gel chromatography to obtain 60.8 g of white crystals (yield: 29.9percent). Melting point: 101.5°-102.5° C.

Reference： [1] Patent: US4986846, 1991, A,
[2] Pesticide Science, 1996, vol. 47, # 2, p. 103 - 114

3
[ 13223-25-1 ]
[ 13223-43-3 ]

Reference： [1] Organic Process Research and Development, 2006, vol. 10, # 6, p. 1167 - 1171

4
[ 20277-69-4 ]
[ 13223-25-1 ]
[ 113583-35-0 ]

Reference： [1] Tetrahedron, 2000, vol. 56, # 27, p. 4739 - 4745

[ 13223-25-1 ] Synthesis Path-Downstream 1~108

1
[ 13223-25-1 ]
[ 128276-49-3 ]
[ 5270-94-0 ]

Reference： [1]Tetrahedron,1999,vol. 55,p. 405 - 412

2
[ 6358-06-1 ]
[ 13223-25-1 ]
2-chloro-5-(4,6-dimethoxy-pyrimidin-2-ylamino)-phenol [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 668 - 671

3
[ 110-85-0 ]
[ 13223-25-1 ]
[ 106615-46-7 ]

Yield	Reaction Conditions	Operation in experiment
65%	With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 10h;	Step 5) 4,6-dimethoxy-2-(piperazin-l-yl)pyrimidine To a mixture of <strong>[13223-25-1]2-<strong>[13223-25-1]chloro-4,6-dimethoxypyrimidine</strong></strong> (1.26 g, 7.2 mmol) in DMF (10 mL) were added potassium carbonate (1.00 g, 7.2 mmol) and anhydrous piperazine (1.24 g, 14.4 mmol). The reaction mixture was heated to 100 C and stirred for 10 hours. Then the reaction mixture was cooled to rt, diluted with water (10 mL) and extracted with EtOAc (20 mL x 3). The combined organic phases were dried over anhydrous Na2S04, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (CLLC /MeOH (v/v) = 20/1) to give the title compound as yellow oil (1.05 g, 65.0%). The compound was characterized by the following spectroscopic data: LC-MS (ESI, pos. ion) m/z: 225.1 [M + H]+ and lH NMR (CDC13, 400 MHz) delta (ppm): 5.39 (s, 1H), 3.86 (s, 6H), 3.78 (t, J= 4.9 Hz, 4H), 3.47 (t, J = 5.0 Hz, 4H).

Reference： [1]Arzneimittel-Forschung/Drug Research,2006,vol. 56,p. 673 - 677
[2]Patent: WO2015/14256,2015,A1 .Location in patent: Paragraph 00189
[3]Journal of Chemical Research,2006,p. 809 - 811

4
[ 87120-72-7 ]
[ 13223-25-1 ]
[ 951004-26-5 ]

Yield	Reaction Conditions	Operation in experiment
30%	In N,N-dimethyl-formamide; at 100℃; for 48h;	A mixture of <strong>[13223-25-1]2-chloro-4,6-dimethoxy-pyrimidine</strong> (3.35 g, 19.19 mmol, 1.0 equiv; commercially available) and 4-amino-piperidine-1-carboxylic acid tert-butyl ester (5.0 g, 24.94 mmol, 1.3 equiv; commercially available) in anhydrous DMF (100 mL) was heated to 100 C. for 48 h. The organic phase was concentrated under reduced pressure and the residue extracted with ethyl acetate (3*50 mL) from a solution of 1 M NaOH (100 mL). The combined organic phases were dried over MgSO4 and the product purified by silica column chromatography using a MPLC system (CombiFlash Companion, Isco Inc.) eluding with a gradient of heptane/ethyl acetate providing 1.97 g (30%) of the title compound. MS (ISP): 339.3 [M+H]+.

Reference： [1]Patent: US2007/225271,2007,A1 .Location in patent: Page/Page column 34-35

5
[ 939052-79-6 ]
[ 13223-25-1 ]
C₁₆H₁₅N₃O₂ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2987 - 2991

6
[ 13223-25-1 ]
1-[4-(4,6-dimethoxypyrimidin-2-yl)piperazin-1-yl]methyl}-1H-benzo[d][1,2,3]triazole [ No CAS ]

Reference： [1]Journal of Chemical Research,2006,p. 809 - 811

7
[ 13223-25-1 ]
7-{4-[4-(4,6-dimethoxy-2-pyrimidinyl)-1-piperazinyl]butoxy}-3,4-dihydro-2(1H)-quinolinone [ No CAS ]

Reference： [1]Arzneimittel-Forschung/Drug Research,2006,vol. 56,p. 673 - 677

8
[ 13223-25-1 ]
[ 478010-75-2 ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 3362 - 3367

9
[ 13223-25-1 ]
[ 478010-74-1 ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 3362 - 3367

10
[ 13223-25-1 ]
5-(3,3,6-trimethyl-indan-5-yloxy)-furan-2-carboxylic acid [4,6-dimethoxy-2-(3-morpholin-4-yl-propylamino)-pyrimidin-5-yl]-amide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 3362 - 3367

11
[ 13223-25-1 ]
[ 654075-29-3 ]

Reference： [1]Organic Letters,2004,vol. 6,p. 277 - 279

12
[ 13223-25-1 ]
2-ethynyl-4-methoxy-5,6,7,8-tetrahydro-10-oxa-1,3-diazaphenanthren-9-one [ No CAS ]

Reference： [1]Organic Letters,2004,vol. 6,p. 277 - 279

13
[ 13223-25-1 ]
[ 654075-28-2 ]

Reference： [1]Organic Letters,2004,vol. 6,p. 277 - 279

14
[ 13223-25-1 ]
7-(4,6-dimethoxy-pyrimidine-2-sulfinyl)-3-methyl-3<i>H</i>-isobenzofuran-1-one [ No CAS ]

Reference： [1]Pest Management Science,2001,vol. 57,p. 205 - 224

15
[ 13223-25-1 ]
methyl 2-(4,6-dimethoxypyrimidin-2-yloxy)-3,3-dimethylbutanoate [ No CAS ]

Reference： [1]Tetrahedron,2000,vol. 56,p. 4739 - 4745
[2]Tetrahedron,2000,vol. 56,p. 4739 - 4745

16
(2R*,4S*)-4-amino-2-ethyl-6-methoxy-3,4-dihydro-2H-[1,5]naphthyridine-1-carboxylic acid ethyl ester [ No CAS ]
[ 13223-25-1 ]
(2R*,4S*)-4-(4,6-dimethoxypyrimidin-2-yl)amino-2-ethyl-6-methoxy-3,4-dihydro-2H-[1,5]naphthyridine-1-carboxylic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; for 48h;Heating / reflux;	A mixture of (2R, 4S) -4-amino-2-ethyl-6-methoxy-3, 4-dihydro-2H- [1, 5] naphthyridine-l-carboxylic acid ethyl ester (300 mg), 2-chloro-4,6- dimethoxypyrimidin (468 mg), N, N-diisopropylethylamine (0.467 ml) and 1,4-dioxane (5 ml) is heated under reflux for 2 days. The reaction solution is concentrated under reduced pressure, and the resulting residue is purified by column chromatography (silica gel; hexane: ethyl acetate = 80 : 20-60 : 40) to give (2R, 4S)-4- (4, 6-dimethoxypyrimidin-2-yl) amino-2- ethyl-6-methoxy-3, 4-dihydro-2H- [1, 5] naphthyridine-1-carboxylic acid ethyl ester (280 g). MS (m/z) : 418 [M+H] +

Reference： [1]Patent: WO2005/95395,2005,A2 .Location in patent: Page/Page column 151-152

17
[ 223514-09-8 ]
[ 223512-08-1 ]
[ 13223-25-1 ]
N-(4-((4-(4,6-Dimethoxypyrimidin-2-yl)piperazin-1-yl)methyl)phenylmethyl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In acetonitrile;	Example 91 Synthesis of N-(4-((4-(4,6-Dimethoxypyrimidin-2-yl)piperazin-1-yl)methyl)phenylmethyl)acetamide (Another Method) A solution of N-(4-((piperazin-1-yl)methyl)phenylmethyl)acetamide (5.0 g) obtained in Example 88(2), <strong>[13223-25-1]2-<strong>[13223-25-1]chloro-4,6-dimethoxypyrimidine</strong></strong> (3.9 g) and potassium carbonate (4.2 g) in acetonitrile (50 ml) was refluxed under heating for 5 hr. The reaction mixture was poured into ice water and extracted with ethyl acetate. The extract was washed with brine and dried over anhydrous sodium sulfate. The solvent was evaporated to give a pale-brown solid. The obtained pale-brown solid was purified by silica gel column chromatography (developing solvent; chloroform:methanol=9:1) and crystallized from diisopropyl ether to give the title compound (5.0 g) as white crystals. 1H-NMR(DMSO-d6)delta: 1.87(3H, s), 2.40-2.50(4H, m), 3.45-3.60(2H, m), 3.65-3.75(4H, m), 3.78(6H, s), 4.24(2H, d, J=5.9 Hz), 5.39(1H, s), 7.20-7.30(4H, m), 8.32(1H, t, J=5.3 Hz).

Reference： [1]Patent: US6455528,2002,B1

18
[ 7688-25-7 ]
[ 13223-25-1 ]
methyl 4,6-dimethoxypyrimidine-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium acetate;dichlorobis(triphenylphosphine)palladium[II]; In tetrahydrofuran; methanol;	EXAMPLE 1 Methyl 4,6-dimethoxy-2-pyrimidinecarboxylate (I, R=Me, R1 =R3 =OMe, and R2 =H) 3.49 g (20 mmol) of <strong>[13223-25-1]2-<strong>[13223-25-1]chloro-4,6-dimethoxypyrimidine</strong></strong> (prepared according to European Published Patent Application No. 0582288), 256 mg (0.6 mmol) of 1,4-bis(diphenylphosphino)butane, 28 mg (40 mumol) of dichlorobis(triphenylphosphine)palladium(II), 4.92 g (60 mmol) of sodium acetate, 1.92 g (60 mmol) of methanol and 56 ml of tetrahydrofuran were introduced into an indirectly heated (oil bath) metal autoclave. The autoclave was flushed several times with carbon monoxide, then the carbon monoxide pressure was increased to 15 bar and the reaction mixture was heated for 6 hours at 180 C. bath temperature. A GC analysis of the reaction mixture revealed a yield of 99 percent with a conversion of 100 percent. For the purpose of working-up, the reaction mixture was evaporated down in vacuo and the residue chromatographed on silica gel 60 with hexane/ethyl acetate (1:1). The yield of isolated product was 1.0 g (71 percent) of colorless crystals. Other data concerning the product was: M.p: 129.7-131.1 C. 1 H NMR (CDCl3) delta=6.15 (s, 1H); 4.03 (s, 6H); 4.00 (s, 3H). MS (m/z): 198 (M+); 197; 183; 168; 139; 125; 108; 93.

Reference： [1]Patent: US5869667,1999,A

19
[ 111-87-5 ]
dichlorotris(triphenylphosphine)ruthenium(II) [ No CAS ]
[ 90-02-8 ]
[ 13223-25-1 ]
[ 147353-26-2 ]

Yield	Reaction Conditions	Operation in experiment
17%	With potassium carbonate; In water; N,N-dimethyl-formamide; benzene;	EXAMPLE 3 Synthesis of 2-(4,6-dimethoxypyrimidin-2-yloxy)benzaldehyde di-n-octylacetal (Compound No. 7) To a mixed solvent of 40 ml of n-octanol and 15 ml of benzene, 1 g of salicylaldehyde was added. The mixture was poured into an eggplant-type flask equipped with a SHEALAM cap, followed by purging with nitrogen. After the addition of 0.04 g of dichlorotris(triphenylphosphine)ruthenium, the mixture was reacted under heating at 100 C. for 20 hours. After the completion of the reaction, the reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The residue thus obtained (0.9 g) was dissolved in 10 ml of DMF, followed by the addition of 0.5 g of <strong>[13223-25-1]2-<strong>[13223-25-1]chloro-4,6-dimethoxypyrimidine</strong></strong> and 0.2 g of potassium carbonate. The resulting mixture was reacted under heating at 110 C. for 3 hours. After the completion of the reaction, the reaction mixture was poured into 100 ml of water, followed by extraction three times, with 50 ml each of ethyl acetate. The organic layer was washed, dried and concentrated under reduced pressure. The residue was subjected to chromatography on a silica gel column and then eluated with a 7:3 mixed solvent of n-hexane and ethyl acetate to purify the same, whereby 0.7 g of the target compound, 2-(4,6-dimethoxypyrimidin-2-yloxy)benzaldehyde di-n-octylacetal, was obtained (yield 17%).

Reference： [1]Patent: US5178662,1993,A

20
[ 90225-19-7 ]
[ 13223-25-1 ]
[ 143946-19-4 ]

Yield	Reaction Conditions	Operation in experiment
30%		(2) 7-Chloro-4-(4,6-dimethoxy-2-pyrimidinylthio)quinoline To 15 ml of dimethylimidazolidinone, 0.13 g of 60% sodium hydride and 0.5 g of 7-chloro-4-mercaptoquinoline were added and stirred at 60 C. for 1 hour. Successively, 0.45 g of <strong>[13223-25-1]2-<strong>[13223-25-1]chloro-4,6-dimethoxypyrimidine</strong></strong> was added and stirred at 50-60 C. for 2.5 hours. After finishing the reaction, the reaction mixture was poured into water and extracted 3 times with 100 ml of ethyl acetate. Ethyl acetate layer was washed with water, dried over anhydrous sodium sulfate and distilled off the solvent. The residue was separated by silica gel column chromatography (elude; n-hexane/ethyl acetate= 1/1) to obtain 0.25 g (30% yield) of the desired product 7-chloro-4-(4,6-dimethoxy-2-pyrimidinylthio)quinoline. Melting point was 93.0-94.5 C. NMR(CDCl3)delta: 3.55(6H,s), 5.72(1H,s), 7.51(1H,dd,J=9.5 & 2.2 Hz), 7.80(1H,d,J=4.4 Hz), 8.14(1H,d,J=2.2 Hz), 8.24(1H,d,J=9.5 Hz), 8.92(1H,d,J=4.4 Hz)

Reference： [1]Patent: US5202329,1993,A

Yield	Reaction Conditions	Operation in experiment
57%		The suspension was saturated at -20 to -15 C. with a total 40 g of HCl gas. After 5 hours of HCl introduction, the reaction mixture was heated to 5 to 10 C. and completely concentrated by evaporation on a rotary evaporator. The residue after concentration by evaporation, was taken up in 50 ml of water, stirred and filtered by suction. The filter residue was washed free of chloride 3 times with 50 ml of water and dried overnight in a vacuum at 35 C. 10.12 g of 2-chloro-4,6-dimethoxypyrimidine was obtained as white crystals (GC 98.4%), corresponding to a yield of 57 percent relative to the dimethylpropanediimidate-dihydrochloride used.

22
[ 109-73-9 ]
[ 13223-25-1 ]
[ 150369-68-9 ]

Yield	Reaction Conditions	Operation in experiment
66%	With triethylamine; In toluene;	EXAMPLE 3 Process for the production of 2-N-butylamino-4,6-dimethoxypyrimidine A solution of 1.9 g of <strong>[13223-25-1]2-<strong>[13223-25-1]chloro-4,6-dimethoxypyrimidine</strong></strong> in 30 ml of toluene [from Example 1(b)]was mixed with 2.7 g of butylamine and 3.3 g of triethylamine and maintained during 50 hours at 80 C. After cooling, it was extracted twice with 30 ml of water and then the organic phase was completely concentrated by evaporation. The light yellow oil was distilled at 140 C./1 mbar. 2.1 g of a colorless oil was obtained corresponding to a yield of 66 percent relative to the propenimidate. The content was 98 percent (GC). Other data for the product was: 1 H-NMR (CDCl3, 300 MHz) delta in ppm: 5.4 (s, 1H); 4.95 (b, 1H); 3.85 (s, 6H); 3.4 (q, 2H); 1.55 (m, 2H); 1.4 (m, 2H); 0.95 (t, 3H). Elementary analysis for C10 H17 N3 O2: Found: C=56.9% H=8.5% N=19.6% Calculated: C=56.9% H=8.1% N=19.9%

Reference： [1]Patent: US5266697,1993,A

23
[ 155012-53-6 ]
[ 13223-25-1 ]
methyl 5-(4,6-Dimethoxypyrimidin-2-yl)oxybenzoxazol-4-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
39%	With potassium carbonate; In N,N-dimethyl-formamide;	EXAMPLE 6 Preparation of Methyl 5-(4,6-Dimethoxypyrimidin-2-yl)oxybenzoxazol-4-carboxylate (Compound No. 446) A mixture comprising 0.6 g of methyl 5-hydroxybenzoxazol-4-carboxylate, 0.6 g of <strong>[13223-25-1]2-<strong>[13223-25-1]chloro-4,6-dimethoxypyrimidine</strong></strong> and 0.7 g of potassium carbonate in 30 ml of N,N-dimethylformamide, was heated and stirred at 115 C. for two hours. The mixture was returned to room temperature, then poured into water and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The oily substance thereby obtained was purified by silica gel column chromatography (n-hexane/ethyl acetate=5/1) to obtain 0.4 g (yield: 39%) of the desired compound.

Reference： [1]Patent: US5616537,1997,A

24
[ 20277-69-4 ]
[ 19444-84-9 ]
[ 13223-25-1 ]
[ 127014-63-5 ]

Yield	Reaction Conditions	Operation in experiment
	potassium carbonate; In dichloromethane; water; N,N-dimethyl-formamide;	Preparation of (+/-)-3-(4,6-dimethoxy-2-pyrimidinyloxy)-2-dihydrofuranone 1.75 g (10 mmol) of <strong>[13223-25-1]2-<strong>[13223-25-1]chloro-4,6-dimethoxypyrimidine</strong></strong>, 1.02 g (10 mmol) of alpha-hydroxy-gamma-butyrolactone and 0.26 g (2.5 mmol) of sodium methanesulfinate were heated in the presence of 2.07 g (15.0 mmol) of potassium carbonate in 10 ml of N,N-dimethylformamide to 120 C. with stirring. After 2 hours, the solvent was removed in a rotary evaporator at 70 C./20 mbar. The residue was taken up in 30 ml of water and 30 ml of dichloromethane. After the organic phase had been separated off, the aqueous phase was again extracted with 20 ml of dichloromethane. The combined organic phases was washed with water, dried over magnesium sulfate and evaporated. The title product was obtained in a yield of 0.43 g (15.5 percent of theory) in the form of a pale brown oil (GC content 94 percent). Other data concerning the title compound was: MS: 240; 210; 181; 157.

Reference： [1]Patent: US5840892,1998,A

25
[ 20277-69-4 ]
[ 13223-25-1 ]
[ 119-36-8 ]
[ 110284-90-7 ]

Yield	Reaction Conditions	Operation in experiment
	potassium carbonate; In dichloromethane; water; N,N-dimethyl-formamide;	Preparation of methyl 2-(4,6-dimethoxy-2-pyrimidinyloxy) benzoate 4.38 g (25 mmol) of <strong>[13223-25-1]2-<strong>[13223-25-1]chloro-4,6-dimethoxypyrimidine</strong></strong>, 3.80 g (25.0 mmol) of methyl 2-hydroxybenzoate and 0.66 g (6.3 mmol) of sodium methanesulfinate were heated in the presence of 5.17 g (37.5 mmol) of potassium carbonate in 25 ml of N,N-dimethylformamide to 120 C. with stirring. After 1.5 hours, the solvent was removed in a rotary evaporator at 60 C./20 mbar. The residue was taken up in 30 ml of water and 30 ml of dichloromethane. After the organic phase had been separated off, the aqueous phase was again extracted with 20 ml of dichloromethane. The combined organic phases was washed with water, dried over magnesium sulfate and evaporated. The residue was purified by chromatography on a silica gel column (eluent hexane/ethyl acetate 4:1). The title product was obtained from the product fraction in a yield of 5.76 g (77.0 percent of theory) (GC content 97 percent). The melting point of the title compound was 106.7 C. to 108.3 C.

Reference： [1]Patent: US5840892,1998,A

26
[ 121129-31-5 ]
[ 20277-69-4 ]
[ 13223-25-1 ]
methyl 2-(4,6-dimethoxypyrimidin-2-yloxy)-3,3-dimethylbutanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	potassium carbonate; In dichloromethane; water; N,N-dimethyl-formamide;	Preparation of methyl (+/-)-2-(4,6-dimethoxy-2-pyrimidinyloxy)-3,3-dimethylbutanoate 4.38 g (25 mmol) of <strong>[13223-25-1]2-<strong>[13223-25-1]chloro-4,6-dimethoxypyrimidine</strong></strong>, 3.90 g (25 mmol) of methyl (+/-)-2-hydroxy-3,3-dimethylbutanoate and 0.66 g (6.3 mmol) of sodium methanesulfinate were heated in the presence of 5.17 g (37.5 mmol) of potassium carbonate in 25 ml of N,N-dimethylformamide to 120 C. with stirring. After 2 hours, the solvent was removed in a rotary evaporator at 70 C./20 mbar. The residue was taken up in 30 ml of water and 30 ml of dichloromethane. After the organic phase had been separated off, the aqueous phase was again extracted with 20 ml of dichloromethane. The combined organic phases was washed with water, dried over magnesium sulfate and evaporated. The title product was obtained in a yield of 5.93 g (82.7 percent of theory) in the form of pale yellowish crystals (GC content 99.2 percent). The melting point of the title compound was 104.4 to 107.0 C.

Reference： [1]Patent: US5840892,1998,A

27
[ 824-79-3 ]
[ 103499-39-4 ]
[ 13223-25-1 ]
methyl S-(+)-(4,6-dimethoxy-2-pyrimidinyloxy)-3,3-dimethylbutanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	potassium carbonate; In dichloromethane; water; N,N-dimethyl-formamide;	Preparation of methyl S-(+)-(4,6-dimethoxy-2-pyrimidinyloxy)-3,3-dimethylbutanoate. 1.75 g (10 mmol) of <strong>[13223-25-1]2-<strong>[13223-25-1]chloro-4,6-dimethoxypyrimidine</strong></strong>, 1.49 g (10 mmol) of methyl S-(+)-2-hydroxy-3,3-dimethylbutanoate and 0.45 g (2.5 mmol) of sodium p-toluenesulfinate were heated in the presence of 2.07 g (15 mmol) of potassium carbonate in 10 ml of N,N-dimethylformamide to 120 C. with stirring. After 7 hours, the solvent was removed in a rotary evaporator at 60 C./20 mbar. The residue was taken up in 30 ml of water and 30 ml of dichloromethane. After the organic phase had been separated off, the aqueous phase was again extracted with 20 ml of dichloromethane. The combined organic phases was washed with water, dried over magnesium sulfate and evaporated. The residue was purified by chromatography on a silica gel column (eluent hexane/ethyl acetate 4:1). The title product was obtained from the product fraction in the form of pale yellowish crystals in a yield of 1.6 g (56.3 percent of theory) (GC content 99 percent). The melting point of the title product was 111.4 to 114.8 C.

Reference： [1]Patent: US5840892,1998,A

28
[ 23287-26-5 ]
[ 20277-69-4 ]
[ 13223-25-1 ]
methyl 2-(4,6-dimethoxypyrimidin-2-yloxy)-3-methylbenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	potassium carbonate; In dichloromethane; water; N,N-dimethyl-formamide;	Preparation of methyl 2-(4,6-dimethoxy-2-pyrimidinyloxy)-3-methylbenzoate 4.38 g (25 mmol) of <strong>[13223-25-1]2-<strong>[13223-25-1]chloro-4,6-dimethoxypyrimidine</strong></strong>, 4.17 g (25.0 mmol) of methyl 2-hydroxy-3-methylbenzoate and 0.66 g (6.3 mmol) of sodium methanesulfinate were heated in the presence of 5.17 g (37.5 mmol) of potassium carbonate in 25 ml of N,N-dimethylformamide to 120 C. with stirring. After 8 hours, the solvent was removed in a rotary evaporator at 60 C./20 mbar. The residue was taken up in 30 ml of water and 30 ml of dichloromethane. After the organic phase had been separated off, the aqueous phase was again extracted with 20 ml of dichloromethane. The combined organic phases was washed with water, dried over magnesium sulfate and evaporated. The residue was purified by chromatography on a silica gel column (eluent hexane/ethyl acetate 4:1). The title product was obtained from the product fraction in a yield of 5.23 g (65.8 percent of theory) (GC content 96 percent). The melting point of the compound was 73.8 to 79.1 C. Other data concerning the title compound was: 1 H NMR (DMSO, MHz 400)delta=7.75 (1 H, d); 7.58 (1 H, d); 7.30 (1 H, t); 5.95 (1 H, s); 3.75 (6 H, s); 3.62 (3 H, s); 2.17 (3 H, s). GC/MS: 304; 273, 245

Reference： [1]Patent: US5840892,1998,A

29
[ 62733-99-7 ]
[ 20277-69-4 ]
[ 13223-25-1 ]
[ 113582-63-1 ]

Yield	Reaction Conditions	Operation in experiment
	potassium carbonate; In N,N-dimethyl-formamide;	Preparation of methyl 3-(4,6-dimethoxy-2-pyrimidinyloxy)-2-pyridinecarboxylate 1.75 g (10 mmol) of <strong>[13223-25-1]2-<strong>[13223-25-1]chloro-4,6-dimethoxypyrimidine</strong></strong>, 1.53 g (10 mmol) of methyl 3-hydroxy-2-pyridinecarboxylate and 0.104 g (1.0 mmol) of sodium methanesulfinate were heated in the presence of 2.17 g (15 mmol) of potassium carbonate in 6 ml of N,N-dimethylformamide to 100 C. with stirring. After 5 hours, the solvent was removed in a rotary evaporator at 60 C./20 mbar. The residue was purified by chromatography on a silica gel column (eluent hexane/ethyl acetate 4:1). The title product was obtained from the product fraction in the form of a yellowish oil in a yield of 1.94 g (61 percent of theory) (GC content 92.3 percent). Other data concerning the title compound was: 1 H NMR (DMSO, MHz 400)delta=8.58 (1 H, d); 7.90 (1 H, d); 7.74 (1 H, dd); 6.01 (1 H, s); 3.75 (6 H, s); 3.68 (3 H, s).

Reference： [1]Patent: US5840892,1998,A

30
[ 20277-69-4 ]
[ 513-86-0 ]
[ 13223-25-1 ]
3-(4,6-dimethoxypyrimidin-2-yloxy)-3,3-butan-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	potassium carbonate; In N,N-dimethyl-formamide;	Preparation of (+/-)-3-(4,6-dimethoxy-2-pyrimidinyloxy)-2-butanone 4.38 g (25 mmol) of <strong>[13223-25-1]2-<strong>[13223-25-1]chloro-4,6-dimethoxypyrimidine</strong></strong>, 2.31 g (26.2 mmol) of 3-hydroxy-2-oxobutane and 0.66 g (6.3 mmol) of sodium methanesulfinate were heated in the presence of 5.17 g (37.5 mmol) of potassium carbonate in 25 ml of N,N-dimethylformamide to 120 C. with stirring. After 3 hours, the solvent was removed in a rotary evaporator at 70 C./20 mbar. The residue was purified by chromatography on a silica gel column (eluent hexane/ethyl acetate 4:1). The title product was obtained from the product fraction in the form of a pale yellowish oil in a yield of 4.58 g (80.4 percent of theory) (GC content 99 percent). Other data concerning the title compound was: 1 H NMR (DMSO, MHz 400)delta=5.87 (1 H, s); 5.70 (1 H, q); 3.82 (6 H, s); 2.25 (3 H, s); 1.44 (3 H, d). MS: 226; 211; 183; 157; 139

Reference： [1]Patent: US5840892,1998,A

31
[ 90-02-8 ]
[ 13223-25-1 ]
[ 110284-76-9 ]

Yield	Reaction Conditions	Operation in experiment
75.0%	In water; dimethyl sulfoxide;	REFERENTIAL EXAMPLE 2 Synthesis of 2-(4,6-dimethoxy-2-pyrimidinyloxy)benzaldehyde A 500-ml four-necked flask was charged with a mixture of 105 g (0.6 mole) of <strong>[13223-25-1]2-<strong>[13223-25-1]chloro-4,6-dimethoxypyrimidine</strong></strong>, 79.4 g (0.65 mole) of salicylic aldehyde 48.3 g (0.35 mole) of potassium carbonate and 450 ml of dimethylsulfoxide. The mixture was gradually heated, and stirred at 120 C. for 3 hours. After the reaction mixture was cooled, it was poured into 2 l of water. Through the procedures of benzene extraction, washing with water, drying over anhydrous sodium sulfate and concentration, 156 g of the target product were obtained as a crude oil. It was purified further by silica gel chromatography to obtain 117.1 g of white crystals (yield: 75.0%). Melting point: 76.0-about 76.5 C.

Reference： [1]Patent: US4986846,1991,A

32
methylthioethyl 2,6-dihydroxybenzoate [ No CAS ]
[ 13223-25-1 ]
methylthioethyl 2,6-bis[(4,6-dimethoxypyrimidin-2-yl)oxy]benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In N,N-dimethyl-formamide;	EXAMPLE 9 Preparation of methylthioethyl 2,6-bis[(4,6-dimethoxypyrimidin-2-yl)oxy]benzoate (Compound No. 2) Methylthioethyl 2,6-dihydroxybenzoate (4.5 g) was dissolved in DMF, and 60% sodium hydride (1.6 g) was added thereto. Then, 2 <strong>[13223-25-1]chloro-4,6-dimethoxypyrimidine</strong> (3.5 g) was added thereto, and the mixture was heated and reacted at a temperature within a range of from 90 to 10 C. for two hours. The reaction solution was poured into ice water and then extracted twice with ethyl acetate. The ethyl acetate layer was washed with water and dried over anhydrous sodium sulfate. After removing inorganic substances by filtration, the solvent was distilled off under reduced pressure. The residue was purified by column chromatography to obtain the above identified compound as a colorless viscous liquid. (etaD20: 1.5706).

Reference： [1]Patent: US4906285,1990,A

33
[ 84437-12-7 ]
[ 13223-25-1 ]
[ 113763-46-5 ]

Yield	Reaction Conditions	Operation in experiment
	In N-methyl-acetamide;	EXAMPLE 2 Preparation of methyl 5-cyano-2-(4,6-dimethoxypyrimidin-2-yl)oxy benzoate (Compound No. 53) STR40 <strong>[13223-25-1]2-Chloro-4,6-dimethoxypyrimidine</strong> (0.5 g) was added to a suspension in dimethylformamide (7 ml) of methyl 5-cyanosalicylate (0.5 g) and 35% potassium hydride (0.15 g), and the mixture was reacted for 5 hours under reflux of dimethylformamide. The reaction mixture was poured into a large amount of water, and extracted with ethyl acetate. The extract was washed with water and dried, and the solvent was distilled off under reduced pressure. The residue thus obtained was purified by silica gel column chromatography to obtain the above identified compound as a white crystal (0.17 g). (Melting point: 79-82 C.).

Reference： [1]Patent: US4900352,1990,A

34
[ 1849-55-4 ]
[ 13223-25-1 ]
2-formyl-3-(4,6-dimethoxypyrimidin-2-yl-oxy)-pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In N-methyl-acetamide;	Example 1 Synthesis of 4,6-dimethoxy-2-(2-formyl-3-pyridyloxy)pyrimidine (Compound No. 1) [Step (a)] <strong>[1849-55-4]2-Formyl-3-hydroxypyridin</strong>e (12.3 g) was dissolved in 100 ml of dimethylformamide, followed by the addition of 4.0 g of 60% sodium hydride in small portions. The resultant mixture was stirred at room temperature for a while. After bubbling subsided, 17.5 g of 2-chloro-4,6-dimethoxypyrimidine were added, followed by heating to 100 C. Subsequent to heating at the same temperature for 3 hours, dimethylformamide was recovered under reduced pressure. The residue was fractionated by chromatography on a silica gel column (solvent: n-hexane/ethyl acetate=7/3), whereby 15 g of the target compound, 4,6-dimethoxy-2-(2-formyl-3-pyridyloxy)pyrimidine, were obtained as crystals having 96-98 C. mp. IR (KBr) (cm-1): 2720, 1710. NMR (CDCl3) 3.80(6H,s), 5.81(1H,s), 7.59(1H,dd,J=4.3 Hz,8.1 Hz), 7.68(1H,dd,J=1.6 Hz,8.1 Hz), 8.71(1H,dd,J=1.6 Hz,4.3 Hz), 10.15(1H,s).

Reference： [1]Patent: US5129937,1992,A

35
[ 104217-48-3 ]
[ 13223-25-1 ]
[ 136429-20-4 ]
3-(4,6-dimethoxy-2-pyrimidinyloxy)-2-pyridinecarboxaldehyde diethylacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	In water;	Example 5 Synthesis of 3-(4,6-dimethoxy-2-pyrimidinyloxy)-2-pyridinecarboxaldehyde diethylacetal (Compound No. 3) Step (d)] Sodium hydride (7.0 g) was added under stirring to 300 ml of dimethylimidazolidinone, followed by the gradual addition of 37.5 g of 3-hydroxy-2-pyridinecarboxaldehyde diethylacetal at room temperature. Heat was evolved with bubbling so that the temperature of the mixture arose to 55 C. After the mixture was heated for 1 hour at 90-95 C., 31.6 g of <strong>[13223-25-1]2-<strong>[13223-25-1]chloro-4,6-dimethoxypyrimidine</strong></strong> were added. The reaction mixture was heated at 100-120 C. for 8 hours so that the reaction was brought to completion. The reaction mixture was cooled to room temperature, added with 500 ml of water, and then extracted three times with 700 ml portions of ethyl acetate. The organic layers were combined, washed with water and then dried over anhydrous sodium sulfate. The solvent was then distilled out, whereby 87.4 g of an oily residue were obtained. The residue was purified by silica gel chromatography (n-hexane/ethyl acetate=1:1) so that 54.6 g of 3-(4,6-dimethoxy-2-pyrimidinyloxy)-2-pyridinecarboxaldehyde diethylacetate were obtained (yield: 90%).

Reference： [1]Patent: US5129937,1992,A

36
[ 73406-50-5 ]
[ 13223-25-1 ]
[ 113582-75-5 ]

Yield	Reaction Conditions	Operation in experiment
40%	In N-methyl-acetamide; hexane;	EXAMPLE 2 Preparation of ethyl 3-(4,6-dimethoxypyrimidin-2-yl)oxy picolinate (Compound No. 2) To 0.5 g of 60% sodium hydride, 50 ml of hexane was added, and subjected to decantation. Then, the mixture was suspended in 30 ml of dimethylformamide. To the dimethylformamide suspension, 1.9 g of ethyl 3-hydroxypicolinate was gradually added, and the 2.0 g of <strong>[13223-25-1]2-<strong>[13223-25-1]chloro-4,6-dimethoxypyrimidine</strong></strong> was added. The mixture was heated and stirred at a reaction temperature of from 130 to 140 C. for 4 hours. After cooling, the reaction solution was poured into water, and extracted with ethyl acetate. The extract was washed with water and dried over magnesium sulfate. Ethyl acetate was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain 1.4 g of ethyl 3-(4,6-dimethoxypyrimidin-2-yl)oxy picolinate. (Yield: 40%, pale yellow liquid, refractive index nD20 =1.5389)

Reference： [1]Patent: US4832729,1989,A

37
[ 13223-25-1 ]
(4,6-dimethoxy-2-pyrimidinyl)-trimethylammonium chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With trimethylamine; In 4-methyl-2-pentanone;	Example 4 To a solution prepared by dissolving 1.18 g (0.02 mol) of trimethylamine in 20 ml of methyl isobutyl ketone, 0.35 g (2.0 mmol) of <strong>[13223-25-1]2-<strong>[13223-25-1]chloro-4,6-dimethoxypyrimidine</strong></strong> was added and the mixture was stirred to produce (4,6-dimethoxy-2-pyrimidinyl)-trimethylammonium chloride in the reaction system.

Reference： [1]Patent: EP700907,1996,A1

38
[ 13223-25-1 ]
[ 57235-35-5 ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; water;	Reference Example 1 Preparation of 4,6-dimethoxy-2-mercaptopyrimidine <strong>[13223-25-1]2-Chloro-4,6-dimethoxypyrimidine</strong> (2.0 g) and sodium hydosulfide (2.30 g) were dissolved in methanol (40 ml), and the resulting solution was heated under reflux for 12 hours. After cooling, the solvent was distilled off under reduced pressure, and water was added. Thereafter, an extraction operation was carried out by using ether. The ether layer was dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure to give <strong>[13223-25-1]2-<strong>[13223-25-1]chloro-4,6-dimethoxypyrimidine</strong></strong> (1.30 g). mp. 101-102C. Thereafter, the aqueous layer was acidified with concentrated hydrochloric acid to pH 2, and the resultant precipitate was separated by filtration, and dried to give 4,6-dimethoxy-2-mercaptopyrimidine (0.48 g). Yield: 24%
	With sodium hydrogensulfide; In methanol;	Reference Example 2 Preparation of 4,6-dimethoxy-2-mercaptopyrimidine <strong>[13223-25-1]2-Chloro-4,6-dimethoxypyrimidine</strong> (2.0 g) and sodium hydrosulfide (2.30 g) were dissolved in methanol, and the resulting solution was stirred at room temperature for 3 hours. The solvent was distilled off under reduced pressure, and the residue thus obtained was admixed with water. An extraction operation was carried out by using ether. The ether layer was dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure to give <strong>[13223-25-1]2-<strong>[13223-25-1]chloro-4,6-dimethoxypyrimidine</strong></strong> (1.95 g). mp. 101-102C. The aqueous layer was acidified with concentrated hydrochloric acid to pH 2, and the crystalline material thus formed was separated by filtration, and dried to give 4,6-dimethoxy-2-mercaptopyrimidine (0.01 g). Yield: 0.5%.

Reference： [1]Patent: EP571856,1993,A1
[2]Patent: EP571856,1993,A1

39
[ 894400-12-5 ]
[ 540-38-5 ]
[ 13223-25-1 ]
[ 894400-16-9 ]

Yield	Reaction Conditions	Operation in experiment
		Reference Example 9 2-(4-Iodophenoxy)-4,6-dimethoxypyrimidine In the same manner as in Reference Example 8, 4-iodophenol (223 mg) and <strong>[13223-25-1]2-<strong>[13223-25-1]chloro-4,6-dimethoxypyrimidine</strong></strong> (192 mg) were reacted by using sodium hydride to obtain 2-(4-iodophenoxy)-4,6-dimethoxypyrimidine (322 mg).

Reference： [1]Patent: EP1840121,2007,A1

40
[ 540-37-4 ]
[ 13223-25-1 ]
[ 894400-90-9 ]

Yield	Reaction Conditions	Operation in experiment
		(1) In the same manner as in Reference Example 24-(1), 4-iodoaniline (220 mg) and <strong>[13223-25-1]2-<strong>[13223-25-1]chloro-4,6-dimethoxypyrimidine</strong></strong> (200 mg) were reacted in the presence of sodium hydride to obtain N-(4-iodophenyl)-4,6-dimethoxypyrimidin-2-amine (141 mg).

Reference： [1]Patent: EP1840121,2007,A1

41
[ 13518-40-6 ]
[ 13223-25-1 ]
C₁₅H₂₅N₃O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
44%	With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 130℃; for 48h;	Example 5; Preparation of Compound 5: N-(4,6-dimethoxy-2-pyrimidinyl)valyl-(4R)-N-((1R,2S)-1-((cyclopropylsulfonyl)carbamoyl)-2-vinylcyclopropyl)-4-((6-methoxy-1-isoquinolinyl)oxy)-L-prolinamide; Step 1:; To a mixture of valine tert-butyl ester hydrochloride (1.55 g, 7.39 mmol) and DIEA (2.01 g, 15.5 mmol) in acetonitrile (37 mL) was added <strong>[13223-25-1]2-<strong>[13223-25-1]chloro-4,6-dimethoxypyrimidine</strong></strong> (1.55 g, 8.87 mmol). The mixture was heated to 130 C. in a Chemglass pressure vessel for 48 hours. Solvent was removed and the viscous brown residue was dissolved in ethyl acetate (100 mL) and the solution was washed with 1.0M aqueous HCl (2×25 mL). The aqueous extracts were combined and back-extracted with ethyl acetate (50 mL), and the organic phases were combined and washed with 10% aqueous sodium carbonate and then with brine. The organic phase was dried over anhydrous MgSO4, filtered and concentrated to a brown oil which was purified by flash silica gel chromatography (step gradient 9:1 hexanes:ethyl acetate then 1:1 hexanes:ethyl acetate) to give the product as a brown viscous oil (1.02 g, 44% yield).

Reference： [1]Patent: US2008/119461,2008,A1 .Location in patent: Page/Page column 42-43

42
[ 98961-97-8 ]
[ 13223-25-1 ]
[ 1146543-70-5 ]

Yield	Reaction Conditions	Operation in experiment
81%	With triethylamine; In tetrahydrofuran; for 40h;Heating / reflux;	Synthesis of 1-N,N'-dimethylsulfamoyl-4-(4,6-dimethoxy-2-pyrimidyl)piperazine (JHX-5) Et3N (0.73 mL, 5.2 mmol) was added to 1.0 g of piperazine-1-sulfonic acid dimethylamide (5.2 mmol) in 20 mL of THF. <strong>[13223-25-1]2-<strong>[13223-25-1]chloro-4,6-dimethoxypyrimidine</strong></strong> (0.9 g, 5.2 mmol) in 5 mL of THF was then added and the mixture was refluxed with stirring for 40 hours. After cooling, THF was removed under vacuum and the remaining yellow solid was dissolved in 300 mL of CHCl3, washed with brine, dried over Na2SO4 and filtered. Solvent removal and CC with 1:1 CHCl3:hexane gave 1.4 g (81%) of white JHX-5, mp 103-105 C. The structure was confirmed by 1H-NMR, 13C-NMR, EI-MS, and elemental analysis. 1H NMR (CDCl3) delta5.41 (s, 1H), 3.86 (s, 6H), 3.89-3.86 (m, 4H), 3.28 (appt, J=4.88 Hz, 4H), 2.86 (s, 6H); EI-MS (m/z) 331 (M+).

Reference： [1]Patent: US2009/105269,2009,A1 .Location in patent: Page/Page column 10
[2]Journal of Medicinal Chemistry,2010,vol. 53,p. 1117 - 1127

43
[ 13223-25-1 ]
2-chloro-5-hydroxy-4,6-dimethoxypyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93.4%		To a stirred suspension of 10.44 g 2-chloride-4,6-dimethoxypyrimidine (60 mmol) in 200 mL of THF under argon at -78 C. was added drop-wise a solution of LDA (2 M in THF/heptane/ethyl benzene, 60 mL, 120 mmol). To a separate round-bottomed flask -78 C. under argon containing t-butyl hydroperoxide (5.5 M in decane, 22.7 mL, 125 mmol) in 150 mL of THF was added a solution of n-BuLi (1.6 M in hexane, 78 mL, 125 mmol). Then, after stirring for 1 hour, the hydroperoxide anion solution was added via a double-ended needle to the aromatic anion. The temperature was gradually raised to 0 C. with stirring continued an additional 3 hours. The reaction was quenched with 6N HCl untie a pH of 7 was obtained. After THF evaporation the remaining aqueous layer was extracted with CHCl3. The CHCl3 layers were washed with brine, dried over Na2SO4, and filtered. Removal of solvent and subsequent purification by CC using 10:1 hexane:EtOAc gave 10.67 g (93.4%) of a white solid. The structure was confirmed by 1H-NMR and 13C-NMR. 1H NMR (CDCl3) delta 4.93 (s, 1H), 4.05 (s, 6H). 13C NMR (CDCl3) 158.1, 146.7, 123.0, 55.1.

Reference： [1]Patent: US2009/105269,2009,A1 .Location in patent: Page/Page column 11
[2]Journal of Medicinal Chemistry,2010,vol. 53,p. 1117 - 1127

44
[ 352553-22-1 ]
[ 13223-25-1 ]
N-(4,6-dimethoxypyrimidin-2-yl)-6-methyl-2,3,4,9-tetrahydro-1H-carbazol-1-amine hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
12 mg (8%)		Example 31 N-(4,6-Dimethoxypyrimidin-2-yl)-6-methyl-2,3,4,9-tetrahydro-1H-carbazol-1-amine Hydrochloride N-(4,6-Dimethoxypyrimidin-2-yl)-6-methyl-2,3,4,9-tetrahydro-1H-carbazol-1-amine hydrochloride was prepared from 6-methyl-2,3,4,9-tetrahydro-1H-carbazol-1-amine and <strong>[13223-25-1]2-<strong>[13223-25-1]chloro-4,6-dimethoxypyrimidine</strong></strong> in a similar manner as described in Example 22 to give 12 mg (8%) of a redish solid. 1H-NMR (CDCl3): delta 10.4 (s, 1H), 7.40 (s, 1H), 7.13 (m, 2H), 6.82 (s, 1H), 5.46 (d, 1H), 5.30 (s, 1H), 4.08 (s, 6H), 2.65 (m, 2H), 2.33 (s, 3H), 2.06 (m, 2H), 1.80 (m, 2H); MS m/z 339 (M+1).

Reference： [1]Patent: US2009/156621,2009,A1

45
[ 1181975-94-9 ]
[ 13223-25-1 ]
[ 1181975-21-2 ]

Yield	Reaction Conditions	Operation in experiment
67.0%		To a solution of methyl 9-[3-(methylamino)propyl]-2,3,4,9-tetrahydro-lH- carbazole-6-carboxylate (200 mg, 0.67 mmol) in DMF (10 ml) was added /-Pr2NEt (0.15 ml, 0.83 mmol). The resulting solution was stirred at room temperature for 10 min and followed by addition of <strong>[13223-25-1]2-<strong>[13223-25-1]chloro-4,6-dimethoxypyrimidine</strong></strong> (97 mg, 0.56 mmol).. The reaction mixture was heated to 80 0C overnight, poured into H2O (30 ml), and extracted with EtOAc (3 x 30 ml). The organic layers were combined, dried over MgSO4, filtered and cone, in vacuo. The crude product was purified by silica gel flash chromatography (EtOAc/hexane, 0-40%) to give the title compound (colorless oil, 163 mg). The yield: 67.0%.

Reference： [1]Patent: WO2009/103022,2009,A1 .Location in patent: Page/Page column 57

46
[ 1181975-06-3 ]
[ 13223-25-1 ]
[ 1181975-20-1 ]

Yield	Reaction Conditions	Operation in experiment
45.9%		To a solution of methyl 9-(3-hydroxypropyl)-2,3,4,9-tetrahydro-lH-carbazole-6- carboxylate (30 mg, 0.10 mmol) in DMF (2 ml) was added NaH (60% in mineral oil, 5 mg, 0.13 mmol). The resulting mixture was stirred at room temperature for 10 min and followed by addition of <strong>[13223-25-1]2-<strong>[13223-25-1]chloro-4,6-dimethoxypyrimidine</strong></strong> (15 mg, 0.09 mmol). The reaction mixture was kept stirring at room temperature for 4 h, poured into H2O (20 ml), and extracted with EtOAc (3 x 20 ml). The organic layers were combined, dried over MgSO4, filtered and cone, in vacuo. The crude product was purified by silica gel flash chromatography (EtOAc/hexane, 0-20%) to give the title compound (white solid, 17.0 mg). The yield: 45.9%.

Reference： [1]Patent: WO2009/103022,2009,A1 .Location in patent: Page/Page column 55

47
[ 41979-39-9 ]
[ 13223-25-1 ]
[ 1246443-54-8 ]

Yield	Reaction Conditions	Operation in experiment
		Example 7; Preparation of 2-hydroxymethyl-8-(4,6-dimethoxy-pyrimidin-2-yl)-l ,4-dioxa-8- azaspiro[4,5]decane (starting material for the preparation of Compound-7); 25 g of piperdone hydrochloride was slowly added in lots to 2g of TBAB and 67g of K2CO3 in 250 ml of acetonitrile at 50-60 (provide exact value), then 25 g of piperdone hydrochloride was slowly added in lots and the reaction mixture stirred for I hr. 29 g of 4,6-dimethoxy-2- chloropyrimidine was added slowly over a period of I hr and the reaction mixture was refluxed for 1 1 hours at 600C.The reaction mixture was neutralized with aq.NaOH solution and extracted with MDC, (methylene dichloride). Organic layer was distilled off to get l -(4-6-dimcthoy- pyrimidin-2-yl)-piperidin-4-one.45g of l -(4-6-dimethoxy-pyrimidin-2-yl)-piperidin-4-one. and 5.2 g of PTSA were stirred in toluene (400 ml) for half an hour. 21 g Glycerol ( 1.2 mole) was added drop wise and the reaction mixture was refluxed at 120 C for 7 hours. Toluene was removed to get the desired product with 85% yield.
		25 g of piperidone hydrochloride was slowly added in lots to 2 g of TBAB and 67 g of K2CO3 in 250 ml of acetonitrile at 50-60 (provide exact value), then 25 g of piperidone hydrochloride was slowly added in lots and the reaction mixture stirred for 1 hr. 29 g of <strong>[13223-25-1]4,6-dimethoxy-2-chloropyrimidine</strong> was added slowly over a period of 1 hr and the reaction mixture was refluxed for 11 hours at 60 C.The reaction mixture was neutralized with aq.NaOH solution and extracted with MDC, (methylene dichloride). Organic layer was distilled off to get 1-(4-6-dimethoxy-pyrimidin-2-yl)-piperidin-4-one.

Reference： [1]Patent: WO2010/109299,2010,A2 .Location in patent: Page/Page column 13
[2]Patent: US2012/225877,2012,A1 .Location in patent: Page/Page column 5

48
[ 62-53-3 ]
[ 13223-25-1 ]
N-phenyl-2-amino-4,6-dimethoxypyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%		To a solution of NaH (60% in oil, 2.1Og, 29 mrnol) in 20 ml_ of anhydrous THF was added aniline (3.0Og, 29 mmol) and the mixture was refluxed for 0.5 hour. After cooling to room temperature, 1 (5,0Og1 29mmol) in 10 ml_ of anhydrous THF was added to the above solution and the resulting reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was then poured into 5OmL of water and extracted with EtOAc {50 ml_ x 3). The combined organic phase was washed with brine and dried over MgSO4 Removal of solvent in vacuo gave 6.Og of crude product which was purified by chromatography (PE/EA =50/1 to 10/1 ).3.50 g of 2 (52%) was obtained as a white solid. LCMS: rn/z = 232.2 (M+ §? 1 ).

Reference： [1]Patent: WO2010/118367,2010,A2 .Location in patent: Page/Page column 38

49
[ 98437-24-2 ]
[ 13223-25-1 ]
[ 1251914-08-5 ]

Yield	Reaction Conditions	Operation in experiment
97%	With (eta3-indenyl)Pd(XPhos)(OTf); potassium carbonate; In tetrahydrofuran; methanol; at 40℃; for 1h;Glovebox; Sealed tube; Cooling with ethanol-dry ice;	In a dinitrogen filled glove box, <strong>[13223-25-1]2-<strong>[13223-25-1]chloro-4,6-dimethoxypyrimidine</strong></strong> (175 1iL, 1.0 mmol), benzofuran-2-boronic acid (243 mg, 1.5 mmol), K2C03 (276 mg, 2.0 mmol) and (3 indenyl)Pd(XPhos)(OTf) (8.4 mg, 0.01 mmol) were added to a 4 dram vial equipped with a magnetic stir bar. Methanol (4 mL) and THF (2 mL) were added to the vial, which was then sealed and stirred outside of the glove box at 40C for one hour. At this point, the vial wasopened to air and diethyl ether (10 mL) and H20 (10 mL) were added to the reaction mixture. The aqueous phase was extracted with diethyl ether (3 x 10 mL). The combined organic phases were dried over MgSO4 and filtered. The supernatant was then passed through a pad of silica gel, followed by removal of the solvent under reduced pressure to give the organic product. Yield: 249 mg, 97%.

Reference： [1]Patent: WO2018/183328,2018,A1 .Location in patent: Page/Page column 40
[2]Journal of the American Chemical Society,2010,vol. 132,p. 14073 - 14075
[3]ACS Catalysis,2015,vol. 5,p. 3680 - 3688

50
[ 109-01-3 ]
[ 13223-25-1 ]
[ 871365-06-9 ]

Yield	Reaction Conditions	Operation in experiment
95%	In N,N-dimethyl-formamide; at 90℃; for 2.5h;Inert atmosphere;	5 g (0.0286 mol) of <strong>[13223-25-1]2-<strong>[13223-25-1]chloro-4,6-dimethoxypyrimidine</strong></strong> (79) and 7.93 niL (7.16 g, 0.0715 mol) of N-methylpiperazine in 22 mL DMF was heated at 90C for 2.5 h. The reaction mixture was concentrated under reduced pressure and the residue was taken up into 200 mL CH2Cl2. This was washed with brine (3 x 50 mL), dried over MgSO4, filtered and concentrated to give 6.51 g (95%) of 80. 1H NMR (500 MHz, CDCl3): delta 5.37 (s, IH), 3.85 (s, 6H), 3.82 (m, 4H), 2.44 (m, 4H), 2.33 (s, 3H); 13C NMR (166 MHz, CDCl3): delta 172.0, 160.8, 77.8, 55.0, 53.4, 46.3, 43.7; MS (mlz): [M+H]+ 239.2.

Reference： [1]Patent: WO2011/22440,2011,A2 .Location in patent: Page/Page column 163
[2]Journal of Medicinal Chemistry,2014,vol. 57,p. 1188 - 1207

51
[ 13223-25-1 ]
[ 1268273-74-0 ]

Reference： [1]Patent: WO2011/22440,2011,A2
[2]Journal of Medicinal Chemistry,2014,vol. 57,p. 1188 - 1207

52
[ 13223-25-1 ]
[ 1268273-75-1 ]

Reference： [1]Patent: WO2011/22440,2011,A2
[2]Journal of Medicinal Chemistry,2014,vol. 57,p. 1188 - 1207

53
[ 13223-25-1 ]
[ 1268273-76-2 ]

Reference： [1]Patent: WO2011/22440,2011,A2
[2]Journal of Medicinal Chemistry,2014,vol. 57,p. 1188 - 1207

54
[ 13223-25-1 ]
[ 1268273-77-3 ]

Reference： [1]Patent: WO2011/22440,2011,A2

55
[ 13223-25-1 ]
[ 1268273-78-4 ]

Reference： [1]Patent: WO2011/22440,2011,A2

56
[ 13223-25-1 ]
[ 1268273-79-5 ]

Reference： [1]Patent: WO2011/22440,2011,A2

57
[ 13223-25-1 ]
C₂₄H₃₄N₆O₅S [ No CAS ]

Reference： [1]Patent: WO2011/22440,2011,A2

58
[ 13223-25-1 ]
[ 1268273-80-8 ]

Reference： [1]Patent: WO2011/22440,2011,A2

59
[ 13223-25-1 ]
[ 1268273-81-9 ]

Reference： [1]Patent: WO2011/22440,2011,A2

60
[ 13223-25-1 ]
[ 1268273-82-0 ]

Reference： [1]Patent: WO2011/22440,2011,A2

61
[ 54582-35-3 ]
[ 13223-25-1 ]
C₁₅H₁₈N₄O₄ [ No CAS ]

Reference： [1]Organic Letters,2011,vol. 13,p. 3262 - 3265

62
[ 13223-25-1 ]
N-(4,6-dimethoxy-2-pyrimidinyl)urea [ No CAS ]

Reference： [1]Organic Letters,2011,vol. 13,p. 3262 - 3265

63
[ 100124-06-9 ]
[ 13223-25-1 ]
[ 1334531-07-5 ]

Reference： [1]Organic Letters,2011,vol. 13,p. 5180 - 5183

64
[ 1181976-15-7 ]
[ 13223-25-1 ]
[ 1181976-13-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 6852 - 6855

65
C₁₉H₂₄N₂O₂ [ No CAS ]
[ 13223-25-1 ]
[ 1350619-15-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 6852 - 6855

66
C₂₀H₂₆N₂O₂ [ No CAS ]
[ 13223-25-1 ]
[ 1350619-16-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 6852 - 6855

67
C₂₀H₂₆N₂O₂ [ No CAS ]
[ 13223-25-1 ]
[ 1350619-17-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 6852 - 6855

68
[ 1181975-72-3 ]
[ 13223-25-1 ]
[ 1181975-10-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 6852 - 6855

69
potassium vinyltrifluoroborate [ No CAS ]
[ 13223-25-1 ]
[ 850234-80-9 ]

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 8428 - 8431
[2]Chemical Communications,2016,vol. 52,p. 3770 - 3772

70
[ 13223-25-1 ]
[ 1375070-81-7 ]
[ 1375070-48-6 ]

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 8428 - 8431

71
[ 1181976-24-8 ]
[ 13223-25-1 ]
[ 1181975-41-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 4955 - 4961

72
C₁₆H₁₉N₃ [ No CAS ]
[ 13223-25-1 ]
[ 1181975-49-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 4955 - 4961

73
[ 42027-81-6 ]
[ 13223-25-1 ]
[ 1394162-01-6 ]

Yield	Reaction Conditions	Operation in experiment
		Step 2: To an ice-cooled solution of 2-(4-nitro-1 H-pyrazol-1-yl)ethanol (1.90 g, 12.02 mmol) in THF (60 mL), NaH (673 mg, 16.82 mmol, 60 %) was added and the solution was stirred for 5 min at 0 C, then the ice bath was removed and the reaction mixture was stirred at rt for 30 min, before <strong>[13223-25-1]2-<strong>[13223-25-1]chloro-4,6-dimethoxypyrimidine</strong></strong> (2.31 g, 13.22 mmol) was added. After 40 min at rt, the reaction mixture was quenched with water and the org. solvent was removed in vacuo. The aq. layer was extracted with DCM (1 x), then acidified with 1 N HCI-solution to pH 2, and extracted with DCM (2x). The combined org. layers were washed with brine, dried (MgS04), filtered and the solvent removed under reduced pressure. Purification by crystallization (DCM-hept-mixture) yielded 4,6-dimethoxy-2-(2-(4-nitro-1 /-/-pyrazol-1- yl)ethoxy)pyrimidine as a beige solid. LC-MS conditions A: tR = 0.88 min, [M+H]+= 295.98.

Reference： [1]Patent: WO2012/110986,2012,A1 .Location in patent: Page/Page column 43

74
[ 1394162-42-5 ]
[ 13223-25-1 ]
[ 1394161-75-1 ]

Yield	Reaction Conditions	Operation in experiment
		General Procedure J: O-ArylationTo a solution of alcohol (1.0 eq.) in THF (0.16 M) was added NaH (1.1 eq.) and stirred at rt for 30 min. To the suspension was added the appropriate 2-chloro-heteroaryl derivative (1.1 eq.) and the resulting mixture was stirred at rt overnight. The mixture was quenched with water and the solvent was removed in vacuo. The aq. layer was extracted with DCM (2x) and the combined org. layers were washed with brine, dried (MgS04), filtered and the solvent was removed under reduced pressure. The residue was purified by FC or prep. HPLC to yield the desired compound.Listed in Table 6 below are example compounds, prepared according to the above- mentioned general procedure F,G,H, I and J from Starting Material and Starting Material B, either readily available or prepared as described above.

Reference： [1]Patent: WO2012/110986,2012,A1 .Location in patent: Page/Page column 38; 79

75
[ 1394162-50-5 ]
[ 13223-25-1 ]
[ 1394161-51-3 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; N-ethyl-N,N-diisopropylamine; In xylene; at 145℃;	General Procedure F: N-Arylation (1 )To a flask was added amine (1 .0 eq.), o-xylene (0.25 M), the appropriate 2-chloro-heteroaryl- derivative (1.0 eq.), K2C03 (3.0 eq.) and DIPEA (3.0 eq.). This suspension was stirred in a sealed flask at 145 C for 1-3 days. The reaction mixture was diluted with EtOAc and water, then the org. layer was separated and the aq. layer was extracted with EtOAc (2x). The combined org. layers were dried (MgS04), filtered and and the solvent was removed under reduced pressure. The residue was purified by FC or prep. HPLC to yield the desired compound. Listed in Table 6 below are example compounds, prepared according to the above- mentioned general procedure F,G,H, I and J from Starting Material and Starting Material B, either readily available or prepared as described above.

Reference： [1]Patent: WO2012/110986,2012,A1 .Location in patent: Page/Page column 76

76
[ 1394162-52-7 ]
[ 13223-25-1 ]
[ 1394161-70-6 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; acetonitrile; at 150 - 180℃;Microwave;	General Procedure H: N-Arylation (3)In a microwave vial, to an amine (1.0 eq.) in MeCN (0.15 M) was added the appropriate 2- chloro-heteroaryl-derivative (1 .0 eq.) and DIPEA (2.5 eq.) followed by NMP (0.03 M). The resulting mixture was heated in the microwave at 150-180 C for 10 min to 1 h. The mixture was directly purified by FC or prep. HPLC to yield the desired compound. Listed in Table 6 below are example compounds, prepared according to the above- mentioned general procedure F,G,H, I and J from Starting Material and Starting Material B, either readily available or prepared as described above.

Reference： [1]Patent: WO2012/110986,2012,A1 .Location in patent: Page/Page column 37; 78

77
[ 1394162-53-8 ]
[ 13223-25-1 ]
[ 1394161-67-1 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 180℃; for 1h;Microwave;	General Procedure G: N-Arylation (2)In a microwave vial, to an amine (1.0 eq.) in MeCN (0.15 M) was added the appropriate 2- chloro-heteroaryl-derivative (1 .0 eq.) and DIPEA (2.5 eq.) The resulting mixture was heated in the microwave at 180 C for 1 h. The mixture was purified by FC or prep. HPLC to yield the desired compound. Listed in Table 6 below are example compounds, prepared according to the above- mentioned general procedure F,G,H, I and J from Starting Material and Starting Material B, either readily available or prepared as described above.

Reference： [1]Patent: WO2012/110986,2012,A1 .Location in patent: Page/Page column 37; 78

78
[ 1394162-58-3 ]
[ 13223-25-1 ]
[ 1394161-84-2 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In acetonitrile; at 180℃; for 0.5h;Microwave;	Example 141rac-A -(1 -((1 -(4,6-dimethoxypyrimidin-2-yl)pyrrolidin-2-yl)methyl)-1 H-pyrazol-4-yl)-5-(m- tolyl)oxazole-4-carboxamideTo a microwave tube was added rac-/V-(1-(pyrrolidin-2-ylmethyl)-1 /-/-pyrazol-4-yl)-5-(m- tolyl)oxazole-4-carboxamide (40 mg, 0.1 1 mmol), <strong>[13223-25-1]2-<strong>[13223-25-1]chloro-4,6-dimethoxypyrimidine</strong></strong> (18 mg, 0.10 mmol) and Cs2C03 (175 mg, 0.228 mmol) in MeCN (0.8 mL). The reaction mixture was irradiated at 180 C for 30 min in the microwave, then the reaction mixture was diluted with DCM (30 mL). The organic layer was separated and washed with H20 (5 mL) and brine (5 mL). The combined organic layers were dried (MgS04), filtered and the solvent was removed under reduced pressure. Purification by FC (hex/ EtOAc 3:7) Rf= 0.4) yielded the title compound (27 mg) as a yellowish solid. LC-MS conditions D: tR = 1 .16 min, [M+H]+= 490.3.

Reference： [1]Patent: WO2012/110986,2012,A1 .Location in patent: Page/Page column 80

79
[ 1394162-11-8 ]
[ 13223-25-1 ]
[ 1394162-12-9 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; potassium carbonate; In 1-methyl-pyrrolidin-2-one; at 20℃; for 0.166667h;Microwave;	Step 3: A microwave tube was charged with 2-(4-nitro-1 /-/-pyrazol-1 -yl)ethanamine (1 .92 g, 5.52 mmol), NMP.(15 mL), <strong>[13223-25-1]2-<strong>[13223-25-1]chloro-4,6-dimethoxypyrimidine</strong></strong> (1 .16 g, 6.62 mmol) and K2C03 (4.19 g, 30.34 mmol). The resulting mixture was heated to 150 C for 20 min in the microwave (no cooling). The reaction mixture was diluted with DCM and washed with water. The org. layer was separated and the aq. layer was extracted with DCM (2x) The combined organic layers were washed with brine, dried (MgS04), filtered and the solvent was removed under reduced pressure. Purification was performed by FC (EtOAc/ hept 6:4) to obtain 4,6- dimethoxy-/V-(2-(4-nitro-1 /-/-pyrazol-1 -yl)ethyl)pyrimidin-2-amine. LC-MS conditions A: tR = 0.33 min, [M+H]+= no ionization.

Reference： [1]Patent: WO2012/110986,2012,A1 .Location in patent: Page/Page column 46-47

80
[ 13223-25-1 ]
[ 1292784-45-2 ]

Reference： [1]Patent: EP2497768,2012,A2

81
[ 13223-25-1 ]
[ 1292784-46-3 ]

Reference： [1]Patent: EP2497768,2012,A2

82
[ 13223-25-1 ]
[ 1292784-47-4 ]

Reference： [1]Patent: EP2497768,2012,A2

83
[ 13223-25-1 ]
[ 1292784-48-5 ]

Reference： [1]Patent: EP2497768,2012,A2

84
[ 13223-25-1 ]
[ 1292784-49-6 ]

Reference： [1]Patent: EP2497768,2012,A2

85
[ 13223-25-1 ]
[ 1292784-50-9 ]

Reference： [1]Patent: EP2497768,2012,A2

86
[ 13223-25-1 ]
[ 1292784-51-0 ]

Reference： [1]Patent: EP2497768,2012,A2

87
[ 13223-25-1 ]
[ 1292784-52-1 ]

Reference： [1]Patent: EP2497768,2012,A2

88
[ 13223-25-1 ]
[ 1246443-56-0 ]

Reference： [1]Patent: US2012/225877,2012,A1

89
[ 13223-25-1 ]
[ 1246443-55-9 ]

Reference： [1]Patent: US2012/225877,2012,A1

90
[ 13223-25-1 ]
[ 1246443-52-6 ]

Reference： [1]Patent: US2012/225877,2012,A1

91
[ 17417-00-4 ]
[ 13223-25-1 ]
[ 127012-42-4 ]

Yield	Reaction Conditions	Operation in experiment
63%	With sodium methansulfinate; potassium carbonate; In N,N-dimethyl-formamide; at 120℃; for 5h;	2-Hydroxy-3-methyl-1-butyric acid methyl ester 1.4g (0.01 mol) and 2-Chloro-4,6-dimethoxy-pyrimidine 1.74g (0.01 mol) were dissolved in DMF (Dimethyl fumarate) 20 ml, K2CO3 2g (1.5 eq) was added thereto, and sodium methane sulfinate 0.26g (0.25 eq) was added thereto, followed by stirring at 120C for 5 hours. The reacted solution was cooled to room temperature, and distilled under reduced pressure to obtain residue. The residue was extracted with cold water and MC three times, the MC layer was dried with MgSO4, and the solvent was removed under reduced-pressure. Through purification with silica gel column chromatography, a target material 1.7g (63%) was obtained.: 1H NMR (300MHz, CDCl3) delta: 1.08(m, 6H), 2.28(m, 1H), 3.71(s, 3H), 3.89(s, 6H), 4.89(d, 1H), 5.71(s, 1H).

Reference： [1]Patent: EP2497768,2012,A2 .Location in patent: Page/Page column 27-28

92
[ 2110-78-3 ]
[ 13223-25-1 ]
[ 1292784-55-4 ]

Yield	Reaction Conditions	Operation in experiment
12%	With sodium methansulfinate; potassium carbonate; In N,N-dimethyl-formamide; at 120℃; for 5h;	Methyl 2-hydroxy isobutyrate 0.52g (0.005 mol) and <strong>[13223-25-1]2-chloro-4,6-dimethoxy-pyrimidine</strong> 0.88g (0.005 mol) were dissolved in DMF 20 ml, K2CO3 0.52g (0.75 eq) was added thereto, and sodium methane sulfate 0.1g was added thereto, followed by stirring at 120C for 5 hours. The reacted solution was cooled to room temperature, and distilled under reduced pressure to obtain residue. The residue was extracted with cold water and ethylacetate three times, and washed with brine twice, the organic layer was dried with MgSO4, and the solvent was removed under reduced-pressure. Through purification with silica gel column chromatography, a target material 0.14g (12%) was obtained.: 1H NMR (300MHz, CDCl3) delta: 1.72(s, 6H), 3.66(s, 3H), 3.93(s, 6H), 5.7(s, 1H).

Reference： [1]Patent: EP2497768,2012,A2 .Location in patent: Page/Page column 28

93
[ 17392-83-5 ]
[ 13223-25-1 ]
[ 1292784-54-3 ]

Yield	Reaction Conditions	Operation in experiment
46%	With sodium methansulfinate; potassium carbonate; In N,N-dimethyl-formamide; at 120℃; for 5h;	D-methyl lactate 0.46g (0.005 mol) and 2-Chloro-4,6-dimethoxy-pyrimidine 0.88g (0.005 mol) were dissolved in DMF 20 ml, K2CO3 0.52g (0.75 eq) was added thereto, and sodium methane sulfate 0.1g was added thereto, followed by stirring at 120C for 5 hours. The reacted solution was cooled to room temperature, and distilled under reduced pressure to obtain residue. The residue was extracted with cold water and ethylacetate three times, and washed with brine twice, the organic layer was dried with MgSO4, and the solvent was removed under reduced-pressure. Through purification with silica gel column chromatography, a target material 0.56g (46%) was obtained.: 1H NMR (300MHz, CDCl3) delta: 1.63(d, 3H), 3.73(s, 3H), 3.89(s, 6H), 5.22(q, 1H), 5.72(s, 1H).

Reference： [1]Patent: EP2497768,2012,A2 .Location in patent: Page/Page column 28

94
[ 27871-49-4 ]
[ 13223-25-1 ]
[ 1292784-53-2 ]

Yield	Reaction Conditions	Operation in experiment
54%	With sodium methansulfinate; potassium carbonate; In N,N-dimethyl-formamide; at 120℃; for 5h;	L-methyl lactate 0.46g (0.005 mol) and 2-Chloro-4,6-dimethoxy-pyrimidine 0.88g (0.005 mol) were dissolved in DMF 20 ml, K2CO3 0.52g (0.75 eq) was added thereto, and sodium methane sulfinate 0.1g was added thereto, followed by stirring at 120C for 5 hours. The reacted solution was cooled to room temperature, and distilled under reduced pressure to obtain residue. The residue was extracted with cold water and ethylacetate (EA) three times, and washed with brine twice, the organic layer was dried with MgSO4, and the solvent was removed under reduced-pressure. Through purification with silica gel column chromatography, a target material 0.66g (54%) was obtained.: 1H NMR (300MHz, CDCl3) delta: 1.63(d, 3H), 3.73(s, 3H), 3.89(s, 6H), 5.22(q, 1H), 5.72(s, 1H).

Reference： [1]Patent: EP2497768,2012,A2 .Location in patent: Page/Page column 28

95
[ 24347-63-5 ]
[ 13223-25-1 ]
[ 133458-61-4 ]

Yield	Reaction Conditions	Operation in experiment
33%	With sodium methansulfinate; potassium carbonate; In N,N-dimethyl-formamide; at 120℃; for 5h;	L-2-hydroxy-3-methyl-butyric acid methyl ester 0.7g (0.0053 mol) and 2-Chloro-4,6-dimethoxy-pyrimidine 0.9g (0.0053 mol) were dissolved in DMF 20 ml, K2CO3 0.6g was added thereto, and sodium methane sulfate 0.1g was added thereto, followed by stirring at 120C for 5 hours. The reacted solution was cooled to room temperature, and distilled under reduced pressure to obtain residue. The residue was extracted with cold water and ethylacetate three times, and washed with brine twice, the organic layer was dried with MgSO4, and the solvent was removed under reduced-pressure. Through purification with silica gel column chromatography, a target material 0.5g (33%) was obtained.: 1H NMR (300MHz, CDCl3) delta: 1.11(m, 7H), 3.71(s, 3H), 3,89(s, 6H), 4.91(d, 1H), 5,71(s, 1H).

Reference： [1]Patent: EP2497768,2012,A2 .Location in patent: Page/Page column 28

96
[ 24347-63-5 ]
[ 13223-25-1 ]
[ 152458-07-6 ]

Reference： [1]Patent: EP2497768,2012,A2

97
[ 4358-87-6 ]
[ 13223-25-1 ]
[ 127091-63-8 ]

Yield	Reaction Conditions	Operation in experiment
57%	With sodium methansulfinate; potassium carbonate; In N,N-dimethyl-formamide; at 120℃; for 5h;	Hydroxyphenyl acetic acid methyl ester 2.3g (0.0138 mol) and 2-Chloro-4,6-dimethoxy-pyrimidine 2.4g (0.0138 mol) were dissolved in DMF 30 ml, K2CO3 2.9g (1.5 eq) was added thereto, and sodium methane sulfinate 0.36g (0.25 eq) was added thereto, followed by stirring at 120C for 5 hours. The reacted solution was cooled to room temperature, and distilled under reduced pressure to obtain residue. The residue was extracted with cold water and MC three times, and the MC layer was dried with MgSO4, and the solvent was removed under reduced-pressure. Through purification with silica gel column chromatography, a target material 2.4g (57%) was obtained.: 1H NMR (300MHz, CDCl3) delta: 3.72(s, 3H), 3.87(s, 6H), 5.75(s, 1H), 6.06(s, 1H), 7.35(m, 3H), 7.59(m, 2H).

Reference： [1]Patent: EP2497768,2012,A2 .Location in patent: Page/Page column 28-29

98
[ 13223-25-1 ]
[ 127010-71-3 ]

Reference： [1]Patent: EP2497768,2012,A2

99
[ 13223-25-1 ]
[ 1292784-56-5 ]

Reference： [1]Patent: EP2497768,2012,A2

100
[ 13223-25-1 ]
[ 1292784-57-6 ]

Reference： [1]Patent: EP2497768,2012,A2

101
[ 13223-25-1 ]
[ 1292784-58-7 ]

Reference： [1]Patent: EP2497768,2012,A2

102
[ 13223-25-1 ]
[ 1292784-59-8 ]

Reference： [1]Patent: EP2497768,2012,A2

103
[ 13223-25-1 ]
[ 1292784-60-1 ]

Reference： [1]Patent: EP2497768,2012,A2

104
[ 13223-25-1 ]
[ 1292784-61-2 ]

Reference： [1]Patent: EP2497768,2012,A2

105
[ 3976-69-0 ]
[ 13223-25-1 ]
[ 1293333-63-7 ]

Yield	Reaction Conditions	Operation in experiment
12%	With sodium methansulfinate; potassium carbonate; In N,N-dimethyl-formamide; at 120℃; for 5h;	D-Methyl 3-hydroxy butyrate 0.52g (0.005 mol) and 2-Chloro-4,6-dimethoxy-pyrimidine 0.88g (0.005 mol) were dissolved in DMF 20 ml, K2CO3 0.52g (0.75 eq) was added thereto, and sodium methane sulfate 0.1g was added thereto, followed by stirring at 120C for 5 hours. The reacted solution was cooled to room temperature, and distilled under reduced pressure to obtain residue. The residue was extracted with cold water and ethylacetate three times, and washed with brine twice, the organic layer was dried with MgSO4, and the solvent was removed under reduced-pressure. Through purification with silica gel column chromatography, a target material 0.15g (12%) was obtained.: 1H NMR (300MHz, CDCl3) delta: 1.43(d, 2H), 1.63(d, 3H), 3.73(s, 3H), 3.89(s, 6H), 5.22(q, 1H), 5.72(s, 1H).

Reference： [1]Patent: EP2497768,2012,A2 .Location in patent: Page/Page column 28

106
[ 13223-25-1 ]
[ 13223-43-3 ]

Reference： [1]Organic Process Research and Development,2006,vol. 10,p. 1167 - 1171

107
[ 250275-15-1 ]
[ 13223-25-1 ]
5-(4,6-dimethoxypyrimidin-2-yl)hexahydropyrrolo[3,4-c]pyrrole-2-carboxylic acid tert-butyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 5620 - 5636

108
[ 76350-90-8 ]
[ 13223-25-1 ]
4,6-dimethoxy-2-((2-methyl-[1,1'-biphenyl]-3-yl)methoxy)pyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%		To a stirred solution of (2-methyl-[l, r-biphenyl]-3-yl)methanol (1 g, 5.05 mmol) in DMF (15 mL) was added NaH (0.24 g, 6.06 mmol) at 0 C and the reaction was stirred for 30 min at room temperature. To the reaction was then added 2- chloro-4,6-dimethoxypyrimidine (0.97 g, 5.55 mmol) in DMF (5 mL) at 0 C and the reaction mixture was stirred at room temperature for 2 h. The reaction mixture was quenched with ice, extracted with ethyl acetate. The organic layer was washed with ice cold water, brine solution and dried over sodium sulphate. The organic layer was then evaporated, the crude was purified on combiflash MPLC using 3% ethyl acetate in hexane as eluent to afford 4,6-dimethoxy-2-((2-methyl-[l,l'-biphenyl]-3- yl)methoxy)pyrimidine as colorless viscous oil (1.4 g, 83%). LCMS (ES) m/z = 337 [M+H]+; lU NMR (400 MHz, DMSO-d6) delta ppm 2.16 (s, 3H), 3.86 (s, 6H), 5.42 (s, 2H), 5.87 (s, 1H), 7.18 (d, =7.2 Hz, 1H), 7.24-7.30 (m, 3H), 7.36-7.37 (m, 1H), 7.39-7.43 (m, 3H).

Reference： [1]Patent: WO2019/87214,2019,A1 .Location in patent: Paragraph 000131

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Technical Information

• Acetal Formation • Acid-Catalyzed α -Halogenation of Ketones • Addition of a Hydrogen Halide to an Internal Alkyne • Alcohols from Haloalkanes by Acetate Substitution-Hydrolysis • Alkyl Halide Occurrence • Alkylation of an Alkynyl Anion • An Alkane are Prepared from an Haloalkane • Chloroalkane Synthesis with SOCI2 • Convert Haloalkanes into Alcohols by SN2 • Esters Are Reduced by LiAlH4 to Give Alcohols • Esters Hydrolyze to Carboxylic Acids and Alcohols • Ether Synthesis by Oxymercuration-Demercuration • Ethers Synthesis from Alcohols with Strong Acids • Friedel-Crafts Alkylation of Benzene with Haloalkanes • General Reactivity • Grignard Reaction • Grignard Reagents Transform Esters into Alcohols • Halogenation of Alkenes • Hiyama Cross-Coupling Reaction • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Methylation of Ammonia • Nomenclature of Ethers • Preparation of Ethers • Primary Ether Cleavage with Strong Nucleophilic Acids • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Ethers • Ring Opening of Oxacyclopropane • Stille Coupling • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • Synthesis of Alcohols from Tertiary Ethers • The Nucleophilic Opening of Oxacyclopropanes

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[ 13223-25-1 ]

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[ CAS No. 13223-25-1 ] {[proInfo.proName]}

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Product Details of [ 13223-25-1 ]

Calculated chemistry of [ 13223-25-1 ] Expand+

Physicochemical Properties

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Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 13223-25-1 ]

Application In Synthesis of [ 13223-25-1 ]

[ 13223-25-1 ] Synthesis Path-Upstream 1~4

[ 13223-25-1 ] Synthesis Path-Downstream 1~108

Technical Information

Related Functional Groups of [ 13223-25-1 ]

Chlorides

Ethers

Related Parent Nucleus of [ 13223-25-1 ]

Pyrimidines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

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Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 13223-25-1 ]

Related Parent Nucleus of
[ 13223-25-1 ]