N,N'-Dimethylurea → 1,3-Dimethyl-5-(trifluoromethyl)dihydropyrimidine-2,4(1H,3H)-dione

HRID 1380426Notes

Reaction equation

[F:1][C:2]([F:9])([F:8])[C:3](=[CH2:7])[C:4](O)=[O:5].[CH3:10][NH:11][C:12]([NH:14][CH3:15])=[O:13].C1CCC(N=C=NC2CCCCC2)CC1>CN(C=O)C>[CH3:10][N:11]1[CH2:7][CH:3]([C:2]([F:9])([F:8])[F:1])[C:4](=[O:5])[N:14]([CH3:15])[C:12]1=[O:13]

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of α-trifluoromethylacrylic acid (700 mg; 5.0 mmoles) and 1,3-dimethylurea (419 mg; 4.8 mmoles) in DMF (5 ml) was cooled to 0° C., and then a solution of DCC (1.21 g; 5.9 mmoles) in DMF (3 ml) was added dropwise. The mixture was stirred at 0° C. for 1 hour. The precipitated solid was filtered off, and washed with ethyl acetate. The solvents were evaporated under reduced pressure from the combined filtrates. The residue was purified by a column chromatography on silica gel to give 566 mg (yield 57%) of 1,3-dimethyl-5-trifluoromethyl-5,6-dihydrouracil (OF-1).

Workup

filtrationThe precipitated solid was filtered off
washwashed with ethyl acetate
customThe solvents were evaporated under reduced pressure from the combined filtrates
customThe residue was purified by a column chromatography on silica gel

Sources & evidence

ORD record: ord-142e95b292f3494399368b17141eba84
Source dataset: uspto-grants-1986_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04581452

Reaction notes

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