1,1-bis(1,1-dimethylethoxy)-N,N,N-trimethylamine → HCID 69449408, compound
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]([C:17](=[O:19])[CH3:18])=[C:15]3[N:10]([C:11]([S:20][CH3:21])=[N:12][CH:13]=[CH:14]3)[N:9]=2)=[CH:4][CH:3]=1.C(O[CH:27](OC(C)(C)C)[N:28]([CH3:30])[CH3:29])(C)(C)C>>[CH3:27][N:28]([CH3:30])/[CH:29]=[CH:18]/[C:17]([C:16]1[C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[N:9][N:10]2[C:15]=1[CH:14]=[CH:13][N:12]=[C:11]2[S:20][CH3:21])=[O:19]Participants
3
Conditions
- Temperature
- 120 °C
Procedure
To 1-[2-(4-fluorophenyl)-7-(methylsulfanyl)pyrazolo[1,5-c]pyrimidin-3-yl]ethanone (1.24 g, 4.12 mmol) was added 1,1-di-tert-butoxy-N,N-dimethylmethanamine (15 mL) and the mixture heated to 120° C. for 1 hour. The reaction was allowed to cool to room temperature and stirred for 16 hours. The mixture was diluted with hexanes. The precipitate was collected by filtration and air dried to yield (2E)-3-(dimethylamino)-1-[2-(4-fluorophenyl)-7-(methylsulfanyl)pyrazolo[1,5-c]pyrimidin-3-yl]prop-2-en-1-one (880 mg, 60%). 1H NMR (DMSO): δ 8.03 (d, 1H), 7.72–7.82 (m, 3H), 7.57 (d, 1H), 7.37 (t, 2H), 5.08 (d, 1H), 3.04 (bs, 3H), 2.71 (s, 3H), 2.52 (bs, 3H). MS m/z 357 (M+1).