Benzaldehyde, 2-hydroxy-3-(2-propenyl)- → 6-[4-(3-Allyl-2-hydroxy-benzyl)-piperazin-1-yl]-3H-pyrimidin-4-one
Reaction equation
[N:1]1([C:7]2[N:12]=[CH:11][NH:10][C:9](=[O:13])[CH:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[CH2:14]([C:17]1[CH:24]=[CH:23][CH:22]=[C:19]([CH:20]=O)[C:18]=1[OH:25])[CH:15]=[CH2:16]>>[CH2:14]([C:17]1[C:18]([OH:25])=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH2:20][N:4]1[CH2:5][CH2:6][N:1]([C:7]2[N:12]=[CH:11][NH:10][C:9](=[O:13])[CH:8]=2)[CH2:2][CH2:3]1)[CH:15]=[CH2:16]Participants
3
Procedure
6-[4-(3-Allyl-2-hydroxy-benzyl)-piperazin-1-yl]-3H -pyrimidin-4-one was prepared using Procedure B from 6-piperazin-1-yl-3H-pyrimidin-4-one (Intermediate 4) and 3-allylsalicylaldehyde (available from Aldrich). 1H NMR (400 MHz, CDCl3) δ 2.58-2.64 (m, 4H), 3.38 (s, 2H), 3.58-3.63 (m, 4H), 3.89 (s, 2H), 5.06-5.15 (m, 2H), 5.39 (s, 1H), 5.97-6.06 (m, 1H), 6.73-6.77 (m, 1H), 6.85-6.89 (m, 1H), 6.99-7.08 (m, 1H), 7.84 (s, 1H), 10.65 (br s, 1H), 12.31 (br s, 1H). Mass spectrum (ES) MH+=327.
Sources & evidence
- ORD record
- ord-12ccd7d9076c46e3a728e039fea643d7
- Source dataset
- uspto-grants-2010_01
- Patent number
- US07652013B2
Reaction notes
Loading…