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

HRID 1182615Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:17])[C:5]([C:14](=O)[CH3:15])=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[CH:8]=1)[CH3:2].C[NH:19][C:20](=[NH:22])[SH:21].S([O-])([O-])(=O)=O.[CH2:28](N(CC)CC)C>C(O)CCC>[CH2:1]([O:3][C:4]([C:5]1[CH:6]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[CH:8]=2)[N:22]=[C:20]([S:21][CH3:28])[NH:19][C:14]=1[CH3:15])=[O:17])[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

3.33 g (13.2 mmol) of 2-acetyl-3-(3-chlorophenyl) acrylic acid ethylester was dissolved in 30 ml of n-butanol. 2.93 g (10.5 mmol) of methylisothiourea-sulfate and 2.00 g (19.8 mmol) of triethylamine were added at room temperature and stirred at 100° C. for one day. After n-butanol was evaporated under reduced pressure, the reaction mixture was diluted with ethyl acetate and washed with saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by the silica gel chromatography (hexane/ethyl acetate=10/1) to obtain the title compound.

Workup

customAfter n-butanol was evaporated under reduced pressure
additionthe reaction mixture was diluted with ethyl acetate
washwashed with saturated aqueous sodium chloride solution
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by the silica gel chromatography (hexane/ethyl acetate=10/1)

Sources & evidence

ORD record: ord-11854ac7b61f43e19f58d40c3a113606
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07288544B2

Reaction notes

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