Diisopropylamine → HCID 10099666, compound
Reaction equation
CS([C:5]1[N:10]=[C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[C:15]([F:20])[CH:14]=2)[C:8]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)=[C:7]([C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:29]=2[Cl:35])[N:6]=1)(=O)=O.[CH:36]([NH:39][CH:40]([CH3:42])[CH3:41])([CH3:38])[CH3:37]>>[CH:36]([N:39]([C:5]1[N:10]=[C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[C:15]([F:20])[CH:14]=2)[C:8]([C:21]2[CH:22]=[CH:23][C:24]([Cl:27])=[CH:25][CH:26]=2)=[C:7]([C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:29]=2[Cl:35])[N:6]=1)[CH:40]([CH3:42])[CH3:41])([CH3:38])[CH3:37]Participants
3
Procedure
2-(Methylsulfonyl)-4-(3,4-difluorobenzyloxy)-5-[4-chlorophenyl]-6-[2,4-dichlorophenyl]pyrimidine (Reference Example 6, 55 mg, 0.10 mmol) was reacted in neat diisopropyl amine heated at 150° C. overnight in a stainless steel pressure bottle by the general procedure described in Example 31, Step A. Workup (excess isopropyl amine removed under reduced pressure) and flash column chromatography on silica gel (eluted with 97/3 hexanes/ethyl acetate) afforded the title compound. HPLC: Rt=4.22 min. 1H-NMR 500 MHz (CDCl3): δ 1.28 (d, J=6 Hz, 6H), 4.217 (q, J=6 Hz, 1H), 5.39 (s, 2H), 7.04 (d, J=8 Hz, 2H), 7.08-7.14 (m, J=2H), 7.17 (m, 5H), 7.31 (d, J=2 Hz, 1H).
Workup
- customWorkup (excess isopropyl amine removed under reduced pressure) and flash column chromatography on silica gel (eluted with 97/3 hexanes/ethyl acetate)