ChemicalBook--->CAS DataBase List--->36745-93-4

36745-93-4

36745-93-4 Structure

36745-93-4 Structure
IdentificationBack Directory
[Name]

2,4-Dichloro-6-methyl-5-pyrimidinecarboxylic acid methyl ester
[CAS]

36745-93-4
[Synonyms]

(3-BROMOPHENYL)(3-PYRIDINYL)METHANONE
(S)-methyl 2-(morpholin-3-yl)acetate HCL
Methyl 2,4-dichloro-6-methyl-5-pyrimidinecarboxylate
Methyl 2,4-dichloro-6-methylpyrimidine-5-carboxylate
2,4-Dichloro-6-methyl-5-pyrimidinecarboxylic acid methyl ester
5-Pyrimidinecarboxylic acid, 2,4-dichloro-6-methyl-, methyl ester
2,4-Dichloro-6-methyl-5-pyrimidinecarboxylic acid methyl ester ISO 9001:2015 REACH
methyl 2,4-dichloro-6-methylpyrimidine-5-carboxylatemethyl 2,4-dichloro-6-methylpyrimidine-5-carboxylate
[Molecular Formula]

C7H6Cl2N2O2
[MDL Number]

MFCD22572319
[MOL File]

36745-93-4.mol
[Molecular Weight]

221.04
Chemical PropertiesBack Directory
[Boiling point ]

292℃
[density ]

1.435
[Fp ]

131℃
[storage temp. ]

under inert gas (nitrogen or Argon) at 2-8°C
[pka]

-3.83±0.39(Predicted)
[Appearance]

White to yellow Solid
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H302-H315-H319-H335
[Precautionary statements ]

P261-P305+P351+P338
Hazard InformationBack Directory
[Uses]

2,4-Dichloro-6-methyl-5-pyrimidinecarboxylic Acid Methyl Ester is used in preparation of 4,6,7-Trisubstituted 1,2-dihydropyrrol[3,4-c]pyridin/pyrimidin-3 -one derivatives useful as Btk kinase inhibitors.
[Synthesis]

Methyl 2,4-dihydroxy-6-MethylpyriMidine-5-carboxylate

869891-41-8

2,4-Dichloro-6-methyl-5-pyrimidinecarboxylic acid methyl ester

36745-93-4

General procedure for the synthesis of methyl 2,4-dichloro-6-methylpyrimidine-5-carboxylate from methyl 2,4-dihydroxy-6-methylpyridine-5-carboxylate: 6-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid methyl ester (1 g, 5.43 mmol) was suspended in POCl3 (10 mL) and N,N-dimethylaniline (10 drops ). The reaction mixture was heated at 105 °C for 6 h until a clarified solution was formed. Upon completion of the reaction, the mixture was cooled to room temperature, concentrated under reduced pressure and subsequently poured into ice water and extracted with ethyl acetate (EtOAc). The organic phases were combined, washed sequentially with water and saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give methyl 2,4-dichloro-6-methylpyrimidine-5-carboxylate (940 mg, 78% yield) as a yellow-green solid. Mass spectrometry analysis: [M + H]+ C7H6Cl2N2O2 calculated value was 222, measured values were 221 and 223.

[References]

[1] Patent: US2011/152273, 2011, A1. Location in patent: Page/Page column 28
[2] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 24, p. 5947 - 5950
[3] Patent: WO2015/131080, 2015, A1. Location in patent: Paragraph 00270; 00274
[4] Patent: US2014/148454, 2014, A1. Location in patent: Paragraph 0676
[5] Patent: WO2014/82739, 2014, A1. Location in patent: Page/Page column 59
Spectrum DetailBack Directory
[Spectrum Detail]

2,4-Dichloro-6-methyl-5-pyrimidinecarboxylic acid methyl ester(36745-93-4)1HNMR
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