Benzenemethanamine, 3,4-dichloro- → N-(3,4-dichlorobenzyl)-2-(2-dimethylsulfamoylphenyl)-5-hydroxy-1-methyl-6-oxo-1,6-dihydropyrimidine-4-carboxamide

HRID 1822726Notes

Reaction equation

HRID 1822726 reaction equation
C([O:3][C:4]([C:6]1[N:7]=[C:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[S:21](=[O:26])(=[O:25])[N:22]([CH3:24])[CH3:23])[N:9]([CH3:14])[C:10](=[O:13])[C:11]=1[OH:12])=O)C.[Cl:27][C:28]1[CH:29]=[C:30]([CH:33]=[CH:34][C:35]=1[Cl:36])[CH2:31][NH2:32]>>[Cl:27][C:28]1[CH:29]=[C:30]([CH:33]=[CH:34][C:35]=1[Cl:36])[CH2:31][NH:32][C:4]([C:6]1[N:7]=[C:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[S:21](=[O:25])(=[O:26])[N:22]([CH3:23])[CH3:24])[N:9]([CH3:14])[C:10](=[O:13])[C:11]=1[OH:12])=[O:3]

Participants

3

Reactant 2

HCID 1608Benzenemethanamine, 3,4-dichloro-HCID 546914412-(2-Dimethylsulfamoyl-phenyl)-5-hydroxy-1-methyl-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid ethyl ester

Product 1

HCID 54705663N-(3,4-dichlorobenzyl)-2-(2-dimethylsulfamoylphenyl)-5-hydroxy-1-methyl-6-oxo-1,6-dihydropyrimidine-4-carboxamide

Procedure

Prepared according to the procedure described for example 2 from 2-(2-dimethylsulfamoyl-phenyl)-5-hydroxy-1-methyl-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid ethyl ester (0.076 g, 0.2 mmol) and 3,4-dichlorobenzylamine (0.13 mL, 1.0 mmol). The title product was obtained as white needles (0.0569 g, 56% yield). 1HNMR (500 MHz, CDCl3) δ: 11.93 (1H, s), 7.91 (1H, dd, J=7.32 Hz), 7.74 (1H, t, J=5.80 Hz), 7.72–7.67 (2H, m), 7.38 (2H), d, J=7.93 Hz), 7.32 (1H, d, J=1.83Hz), 7.11 (1H, dd, J=8.24, 1.83 Hz), 4.60 (1H, dd, J=15.26, 7.02 Hz), 4.41 (1H, dd, J=15.26, 5.80 Hz), 3.24 (3H, s), 2.69 (6H, s). HRMS (ESI) calcd for C21H21SCl2N4O5 (M+H): 511.0610; found: 511.0612.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-a1850503974e4433b5561ce642734640
Source dataset
uspto-grants-2006_05
Patent number
US07037908B2

Reaction notes

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