84332-06-9|4-Methoxy-2-(methylthio)-5-pyrimidinecarboxylic acid| Ambeed

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Quality Control of [ 84332-06-9 ] Purity: 95% SDS Specification

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Product Details of [ 84332-06-9 ]

CAS No. :	84332-06-9
Formula :	C₇H₈N₂O₃S
M.W :	200.22
SMILES Code :	COC1=C(C=NC(SC)=N1)C(O)=O
MDL No. :	MFCD02671593
Boiling Point :	No data available
InChI Key :	SXNHLOFNZOTILK-UHFFFAOYSA-N
Pubchem ID :	12829003

Safety of [ 84332-06-9 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H312-H332
Precautionary Statements:	P261-P264-P270-P271-P280-P302+P352-P304+P340-P310-P330-P361-P403+P233-P405-P501

Application In Synthesis of [ 84332-06-9 ]

* 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.

Downstream synthetic route of [ 84332-06-9 ]

[ 84332-06-9 ] Synthesis Path-Downstream 1~24

1
[ 67-56-1 ]
[ 5909-24-0 ]
[ 84332-06-9 ]

Yield	Reaction Conditions	Operation in experiment
66.25%	With sodium hydroxide; at 20℃; for 3h;	To a stirred solution of 5 ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate (3.0 g, 12.893 mmol, 1.0 eq), in 30 MeOH (15 mL) was added 1M solution of 8 NaOH (20 mL) at rt. The resulting mixture was stirred at the same temperature for 3 h. The reaction mixture was concentrated and acidified with 1N HCl solution (10 mL) to adjusted the pH 4-5, the formation of white precipitate was observed which was filtered and dried under vacuum to afford the desired compound 426 4-methoxy-2-(methylthio)pyrimidine-5-carboxylic acid (1.71 g, 66.25%) as white solid. (0498) LCMS: 201.1[M+1]+
	With sodium hydroxide; at 20℃; for 3h;	Weigh ethyl 4-chloro-2-methylthio 5-pyrimidinecarboxylate (2 g, 8.6 mmol) into a 100 mL eggplant-shaped flask, and add 30 mL MeOH and 10 mL 2N NaOH solution sequentially.After stirring at room temperature for 3 hours, most of the methanol was evaporated to dryness, the resulting solution was acidified with 2N dilute hydrochloric acid solution to a pH of 4-5, filtered to obtain a pure white solid, and vacuum dried overnight.Without further purification directly to the next step.
	With water; sodium hydroxide;	(1) Using ethyl 4-chloro-2-methylthiopyrimidine-5-carboxylate as the starting material, the intermediate (I-1) was obtained in methanol and aqueous sodium hydroxide (J.Med.Chem.2009 , 52, 1081-1099).

References: [1]Patent: US2019/106436,2019,A1 .Location in patent: Paragraph 0496-0498.
[2]Journal of Medicinal Chemistry,2009,vol. 52,p. 1081 - 1099.
[3]Patent: CN111848613,2020,A .Location in patent: Paragraph 0048; 0083; 0084.
[4]Patent: CN113943281,2022,A .Location in patent: Paragraph 0091-0094.

2
[ 84332-06-9 ]
[ 66206-82-4 ]

References: [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 1081 - 1099.

3
[ 84332-06-9 ]
N-(3,5-dichloropyridin-4-yl)-4-hydroxy-2-(methylthio)pyrimidine-5-carboxamide [ No CAS ]

References: [1]Patent: US2019/106436,2019,A1 .

4
[ 84332-06-9 ]
3-(3,5-dichloropyridin-4-yl)-7-(methylthio)-2,3-dihydro-4H-pyrimido[5,4-e][1,3]oxazin-4-one [ No CAS ]

References: [1]Patent: US2019/106436,2019,A1 .

5
[ 84332-06-9 ]
3-(3,5-dichloropyridin-4-yl)-7-((4-(4-methylpiperazin-1-yl)phenyl)amino)-2,3-dihydro-4H-pyrimido[5,4-e][1,3]oxazin-4-one [ No CAS ]

References: [1]Patent: US2019/106436,2019,A1 .

6
[ 22889-78-7 ]
[ 84332-06-9 ]
N-(3,5-dichloropyridin-4-yl)-4-methoxy-2-(methylthio)pyrimidine-5-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75.06%		To a stirred solution of 426 <strong>[84332-06-9]4-methoxy-2-(methylthio)pyrimidine-5-carboxylic acid</strong> (1.7 g, 8.491 mmol, 1.0 eq), in 82 CH2Cl2 (50 mL) was added 429 (COCl)2 (1.45 mL, 16.982 mmol, 2.0 eq) and 47 DMF (0.01 mL) at 0 C. The resulting mixture was stirred at rt for 5 h. The reaction mixture was concentrated, dissolved in CH2Cl2 (5.0 mL) and added to a stirred solution of 430 3,5-dichloropyridin-4-amine (1.385 g, 8.491 mmol, 1.0 eq) and 431 NaH (680 mg, 16.982 mmol, 2.0 eq) in DMF (30 mL) at 0 C. The resulting mixture was stirred at rt for 2 h. The progress of reaction was monitored by LCMS. The reaction mixture was poured in ice cold 7 water (50 mL), extracted with EtOAc (2×100 mL), the combined organic layers were washed with water (50 mL), with brine (50 mL), dried over Na2SO4 concentrated and purified by flash chromatography [silica gel 100-200 mesh elution 0-30% 19 EtOAc in 20 hexane] to afford the desired compound 432 N-(3,5-dichloropyridin-4-yl)-4-methoxy-2-(methylthio)pyrimidine-5-carboxamide (2.2 g, 75.06%) as off white solid. (0500) LCMS: 344.9[M+1]+

References: [1]Patent: US2019/106436,2019,A1 .Location in patent: Paragraph 0496; 0499-0500.

7
[ 67-56-1 ]
[ 84332-06-9 ]
[ 15400-57-4 ]

Yield	Reaction Conditions	Operation in experiment
4.18 g	With thionyl chloride; at 85℃; for 3h;Cooling with ice;	In a mixture of 8.38 g of 4-methoxy-2- (methylthio) pyrimidine-5-carboxylic acid and 90 mL of methanolUnder ice cooling, 9 mL of thionyl chloride was added, and the mixture was stirred at 85 C. for 3 hours. The resulting mixture was allowed to cool to room temperature and concentrated. To the obtained residue was added saturated aqueous sodium bicarbonate solution, and the mixture was extracted with ethyl acetate. The resulting organic layer was dried over anhydrous sodium sulfate and concentrated to give 4.18 g of Intermediate C-1 shown below.
4.18 g	With thionyl chloride; at 85℃; for 3h;Cooling with ice;	To a mixture of <strong>[84332-06-9]4-methoxy-2-(methylthio)pyrimidine-5-carboxylic acid</strong> 8.38 g and methanol 90 mL was added thionyl chloride 9 mL under ice cooling, and the mixture was stirred at 85 C. for 3 hours. The resulting mixture was cooled to room temperature, and concentrated. To the resulting residue was added aqueous saturated sodium hydrogen cardonate solution, and the mixture was extracted with ethyl acetate. The resulting organic layer was dried over anhydrous sodium sulfate, and concentrated to obtain intermediate compound C-1 shown below 4.18 g. Intermediate compound C-1: 1H-NMR (CDCl3) δ: 8.82 (1H, s), 4.10 (3H, s), 3.89 (3H, s), 2.59 (3H, s).

References: [1]Patent: JP2019/65018,2019,A .Location in patent: Paragraph 0449.
[2]Patent: US2020/85051,2020,A1 .Location in patent: Paragraph 230-2331.

8
[ 1071-46-1 ]
[ 84332-06-9 ]
[ 881634-01-1 ]

Yield	Reaction Conditions	Operation in experiment
		4-methoxy-2-(methylthio)-5-pyrimidine carboxylic acid(1.6g, 8mmol)Disperse in methylene chloride (30mL)And place in an ice bath to cool,One drop of DMF and oxalyl chloride (2.3 mL, 25.8 mmol) were added dropwise to the stirring condition.After the addition, continue stirring at room temperature for 4 hours.Evaporate the reaction solvent to obtain a pure white solid,It can be used in the next step without further purification.Under the protection of nitrogen, to the anhydrous THF (15mL) solution of monoethyl malonate (2.3mL, 21.4mmol) in an ice bath was added dropwise methylmagnesium bromide in ether (3M, 14.3mL, 42.9mmol) . After dripping and continuing the reaction for 20 minutes, the above-mentioned acid chloride solution in THF (30 mL) was added dropwise to the reaction system. After stirring at room temperature for 3 hours, the reaction solution was poured into ice water, acidified with a 2N dilute hydrochloric acid solution to a pH of 5-6, and extracted with EA (20 mL*3). The organic phases were combined, washed with saturated brine, dried and concentrated with anhydrous sodium sulfate, and purified by silica gel column chromatography (ethyl acetate: petroleum ether = 1:12).The obtained white solid was recrystallized in ethyl acetate/petroleum ether

References: [1]Patent: CN111848613,2020,A .Location in patent: Paragraph 0048; 0049; 0085-0087.

9
[ 84332-06-9 ]
[ 100426-81-1 ]

References: [1]Patent: CN111848613,2020,A .
[2]Patent: CN111848613,2020,A .

10
[ 84332-06-9 ]
2-(benzylamino)-5-oxo-8-phenyl-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester [ No CAS ]

References: [1]Patent: CN111848613,2020,A .
[2]Patent: CN111848613,2020,A .

11
[ 84332-06-9 ]
5-oxo-8-phenyl-2-(phenylamino)-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester [ No CAS ]

References: [1]Patent: CN111848613,2020,A .
[2]Patent: CN111848613,2020,A .

12
[ 84332-06-9 ]
2-((4-cyanophenyl)amino)-5-oxo-8-phenyl-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester [ No CAS ]

References: [1]Patent: CN111848613,2020,A .
[2]Patent: CN111848613,2020,A .

13
[ 84332-06-9 ]
2-((4-cyanophenyl)amino)-5-oxo-8-phenyl-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid [ No CAS ]

References: [1]Patent: CN111848613,2020,A .
[2]Patent: CN111848613,2020,A .

14
[ 84332-06-9 ]
2-((4-cyanophenyl)amino)-5-oxo-8-phenyl-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxamide [ No CAS ]

References: [1]Patent: CN111848613,2020,A .
[2]Patent: CN111848613,2020,A .

15
[ 84332-06-9 ]
C₁₇H₁₅N₃O₅S [ No CAS ]

References: [1]Patent: CN111848613,2020,A .
[2]Patent: CN111848613,2020,A .

16
[ 84332-06-9 ]
1-(4-methoxy-2-(methylthio)pyrimidin-5-yl)ethan-1-one [ No CAS ]