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-pyridin-4-yl-benzenesulfonamide

HRID 858077Notes

Reaction equation

HRID 858077 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].[N:23]1[CH:28]=[CH:27][C:26]([NH:29][S:30]([C:33]2[CH:38]=[CH:37][C:36]([CH2:39][C:40](O)=O)=[CH:35][CH:34]=2)(=[O:32])=[O:31])=[CH:25][CH:24]=1>>[CH2:9]([N:6]1[C:7]2[N:8]=[C:40]([CH2:39][C:36]3[CH:35]=[CH:34][C:33]([S:30]([NH:29][C:26]4[CH:27]=[CH:28][N:23]=[CH:24][CH:25]=4)(=[O:31])=[O:32])=[CH:38][CH:37]=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

HCID 218917565,6-diamino-1-butyl-3-(2-fluorobenzyl)-1H-pyrimidine-2,4-dioneHCID 43440333[4-(Pyridin-4-ylsulfamoyl)-phenyl]-acetic acid

Product 1

HCID 103706224-[3-Butyl-1-(2-fluoro-benzyl)-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-ylmethyl]-N-pyridin-4-yl-benzenesulfonamide

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-(pyridin-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-pyridin-4-yl-benzenesulfonamide was obtained as a colorless solid; 1H NMR (DMSO-d6, 300 MHz) δH 13.50 (s, 1H), 12.65 (broad s, 1H), 8.00–7.80 (m, 2H), 7.75–7.60 (m, 2H), 7.55–7.35 (m, 2H), 7.30–6.80 (m, 6H), 5.08 (s, 2H), 4.11 (s, 2H), 3.93 (t, J=7.3 Hz, 2H), 1.70–1.50 (m, 2H), 1.35–1.15 (m, 2H), 0.83 (t, J=7.1 Hz, 3H); FAB-HRMS m/e calculated for C28H27FN6O4S (M+H)+ 563.1877, found 563.1858.

Sources & evidence

ORD record
ord-c3ebbfd200ef492e84970c9962d23ca0
Source dataset
uspto-grants-2006_12
Patent number
US07148229B2

Reaction notes

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