5,6-diamino-1-butyl-3-(2-fluorobenzyl)-1H-pyrimidine-2,4-dione → 4-[3-Butyl-1-(2-fluoro-benzyl)-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-ylmethyl]-N-(1,3,5-trimethyl-1H-pyrazol-4-yl)-benzenesulfonamide
Reaction equation
[NH2:1][C:2]1[C:3](=[O:22])[N:4]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[F:21])[C:5](=[O:13])[N:6]([CH2:9][CH2:10][CH2:11][CH3:12])[C:7]=1[NH2:8].[CH3:23][N:24]1[C:28]([CH3:29])=[C:27]([NH:30][S:31]([C:34]2[CH:39]=[CH:38][C:37]([CH2:40][C:41](O)=O)=[CH:36][CH:35]=2)(=[O:33])=[O:32])[C:26]([CH3:44])=[N:25]1>>[CH2:9]([N:6]1[C:7]2[N:8]=[C:41]([CH2:40][C:37]3[CH:38]=[CH:39][C:34]([S:31]([NH:30][C:27]4[C:26]([CH3:44])=[N:25][N:24]([CH3:23])[C:28]=4[CH3:29])(=[O:32])=[O:33])=[CH:35][CH:36]=3)[NH:1][C:2]=2[C:3](=[O:22])[N:4]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[F:21])[C:5]1=[O:13])[CH2:10][CH2:11][CH3:12]Participants
3
Reactant 2
Product 1
Procedure
Prepared from 5,6-diamino-1-butyl-3-(2-fluoro-benzyl)-1H-pyrimidine-2,4-dione (30.6 mg, 0.1 mmol) and [4-(1,3,5-trimethyl-1H-pyrazol-4-ylsulfamoyl)-phenyl]-acetic acid. 4-[3-Butyl-1-(2-fluoro-benzyl)-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-ylmethyl]-N-(1,3,5-trimethyl-1H-pyrazol-4-yl)-benzenesulfonamide was obtained as a colorless solid; 1H NMR (DMSO-d6, 300 MHz) δH 13.48 (s, 1H), 8.94 (s, 1H), 7.49 (d, J=8.4 Hz, 2H), 7.38 (d, J=7.7 Hz, 2H), 7.30–6.90 (m, 4H), 5.03 (s, 2H), 4.10 (s, 2H), 3.88 (t, J=7.1 Hz, 2H), 3.45 (s, 3H), 1.71 (s, 3H), 1.60–1.45 (m, 2H), 1.42 (s, 3H), 1.25–1.10 (m, 2H), 0.79 (t, J=7.5 Hz, 3H); FAB-HRMS m/e calculated for C29H32FN7O4S (M+H)+ 594.2299, found 594.2281.
Sources & evidence
- ORD record
- ord-2479799f46a94090b74e024702ce9b29
- Source dataset
- uspto-grants-2006_12
- Patent number
- US07148229B2
Reaction notes
Loading…