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-3-yl-benzenesulfonamide

HRID 858078Notes

Reaction equation

HRID 858078 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][CH:26]=[C:25]([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: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:25]4[CH:24]=[N:23][CH:28]=[CH:27][CH:26]=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 43440329[4-(Pyridin-3-ylsulfamoyl)-phenyl]-acetic acid

Product 1

HCID 104154424-[3-Butyl-1-(2-fluoro-benzyl)-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-ylmethyl]-N-pyridin-3-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-3-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-3-yl-benzenesulfonamide was obtained as a colorless solid; 1H NMR (DMSO-d6, 300 MHz) δH 13.50 (s, 1H), 10.54 (s, 1H), 8.23 (d, J=14.3 Hz, 2H), 7.71 (d, J=8.1 Hz, 2H), 7.55–7.40 (m, 3H), 7.35–6.95 (m, 5H), 5.08 (s, 2H), 4.13 (s, 2H), 3.92 (t, J=7.3 Hz, 2H), 1.59 (t, J=7.1 Hz, 2H), 1.23 (q, J=7.3 Hz, 2H), 0.83 (t, J=7.5 Hz, 3H); FAB-HRMS m/e calculated for C28H27FN6O4S (M+H)+ 563.1877, found 563.1860.

Sources & evidence

ORD record
ord-01535e5705804d3f80ae359d28da24f8
Source dataset
uspto-grants-2006_12
Patent number
US07148229B2

Reaction notes

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