Dimethylamine → N,N-Dimethyl 1,6-dihydro-6-oxo-2-(2-propoxyphenyl)-pyrimidine-5-carboxamide
Reaction equation
[O:1]=[C:2]1[NH:7][C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[O:14][CH2:15][CH2:16][CH3:17])=[N:5][CH:4]=[C:3]1[C:18]([O:20]CC)=O.[CH3:23][NH:24][CH3:25]>>[CH3:23][N:24]([CH3:25])[C:18]([C:3]1[C:2](=[O:1])[NH:7][C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[O:14][CH2:15][CH2:16][CH3:17])=[N:5][CH:4]=1)=[O:20]Participants
3
Procedure
Ethyl 1,6-dihydro-6-oxo-2-(2-propoxyphenyl)pyrimidine-5-carboxylate (1.5 g, U.S. Pat. No. 4,031,093) was treated with dimethylamine (33% in industrial methylated spirit, 50 ml) in a pressure vessel (414 kPa) at 120° C. for 15 hours. Solvent was removed under reduced pressure affording a yellow oily residue which was washed several times with ether. The volume of the combined ethereal washings was reduced by evaporation to afford on standing overnight a white precipitate (540 mg). This was recrystallised from ether to afford the title compound, 310 mg, m.p. 104°-105° C.
Workup
- customSolvent was removed under reduced pressure
- customaffording a yellow oily residue which
- washwas washed several times with ether
- customThe volume of the combined ethereal washings was reduced by evaporation
- customto afford
- customThis was recrystallised from ether
Sources & evidence
- ORD record
- ord-3db3b29e95084ae3a7ef300fc049a00d
- Source dataset
- uspto-grants-1994_03
- Patent number
- US05290933
Reaction notes
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