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

HRID 1822728Notes

Reaction equation

HRID 1822728 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[CH3:36])[CH2:31][NH2:32]>>[Cl:27][C:28]1[CH:29]=[C:30]([CH:33]=[CH:34][C:35]=1[CH3:36])[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:26])(=[O:25])[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 106225Benzenemethanamine, 3-chloro-4-methyl-HCID 546914412-(2-Dimethylsulfamoyl-phenyl)-5-hydroxy-1-methyl-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid ethyl ester

Product 1

HCID 54681882N-(3-chloro-4-methylbenzyl)-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-chloro-4-methylbenzylamine (0.14 mL, 1.0 mmol). The title product was obtained as white needles (0.0601 g, 61% yield). 1HNMR (500 MHz, CDCl3) δ: 12.05 (1H, s), 7.92 (1H, dd, J=7.47, 1.83 Hz), 7.72–7.66 (3H, m), 7.38 (1H, dd, J=7.17, 2.29 Hz), 7.19 (1H, s), 7.16 (1H, d, J=7.63 Hz), 7.04 (1H, d, J=7.63 Hz), 4.61 (1H, dd, J=14.95, 7.02 Hz), 4.36 (1H, dd, J=14.96, 5.19 Hz), 3.24 (3H, s), 2.66 (6H, s), 2.32 (3H, s). HRMS (ESI) calcd for C22H24ClN4O5S (M+H): 491.1156; found: 491.1159.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-2150ce5cde794d028bb20fd53b0dd8d9
Source dataset
uspto-grants-2006_05
Patent number
US07037908B2

Reaction notes

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