Water → 1,3-Dimethyl-5-(trifluoromethyl)dihydropyrimidine-2,4(1H,3H)-dione

HRID 1380428Notes

Reaction equation

[CH3:1][NH:2][C:3]([NH:5][CH3:6])=[O:4].[F:7][C:8]([F:15])([F:14])[C:9](=[CH2:13])[C:10](Cl)=[O:11].C(N(CC)CC)C.O>CN(C=O)C>[CH3:1][N:2]1[CH2:13][CH:9]([C:8]([F:15])([F:14])[F:7])[C:10](=[O:11])[N:5]([CH3:6])[C:3]1=[O:4]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 1,3-dimethylurea (168 mg; 1.9 mmoles) in DMF (2 ml) was cooled to 0° C., and α-trifluoromethylacryloyl chloride (317 mg; 2.0 mmoles) and triethylamine (0.31 ml; 2.2 mmoles) were added dropwise. The mixture was stirred at 0° C. for 2 hours, and then water (20 ml) was added. The mixture was extracted with methylene chloride (20 ml×1, 10 ml×2). The combined extracts were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by a column chromatography on silica gel (chloroform) to give 197 mg (yield: 49%) of 1,3-dimethyl-5-trifluoromethyl-5,6-dihydrouracil.

Workup

extractionThe mixture was extracted with methylene chloride (20 ml×1, 10 ml×2)
dry with materialThe combined extracts were dried over anhydrous magnesium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was purified by a column chromatography on silica gel (chloroform)

Sources & evidence

ORD record: ord-ea656b1cfe6f4031a690b8264285432f
Source dataset: uspto-grants-1986_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04581452

Reaction notes

Loading…