4-(3-Chlorophenyl)-6-methyl-2-(methylthio)-1,4-dihydropyrimidine-5-carboxylic acid ethylester → 4-(3-Chlorophenyl)-6-methyl-2-(methylthio)-5-pyrimidinecarboxylic acid ethylester

HRID 1727938Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[CH:7]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=2)[N:8]=[C:9]([S:13][CH3:14])[NH:10][C:11]=1[CH3:12])=[O:5])[CH3:2]>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH2:1]([O:3][C:4]([C:6]1[C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=2)=[N:8][C:9]([S:13][CH3:14])=[N:10][C:11]=1[CH3:12])=[O:5])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

2.09 g (6.43 mmol) of 4-(3-chlorophenyl)-6-methyl-2-(methylthio)-1,4-dihydropyrimidine-5-carboxylic acid ethylester was dissolved in 30 ml of chloroform. 8.39 g (96.5 mmol) of manganese dioxide was added at room temperature and stirred at 80° C. for 2 hours. After filtration of insoluble matters, the obtained filtrate was concentrated under reduced pressure. The residue was purified by the silica gel chromatography (hexane/ethyl acetate=10/1) to obtain the title compound.

Workup

filtrationAfter filtration of insoluble matters
concentrationthe obtained filtrate was concentrated under reduced pressure
customThe residue was purified by the silica gel chromatography (hexane/ethyl acetate=10/1)

Sources & evidence

ORD record: ord-4d4ba8c45a6a4f1e967686d17141a34e
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07494989B2

Reaction notes

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