4-Chlorobenzylamine → N-(4-chlorobenzyl)-2-(2,6-difluorophenyl)-5-hydroxy-1-methyl-6-oxo-1,6-dihydropyrimidine-4-carboxamide

HRID 1822685Notes

Reaction equation

HRID 1822685 reaction equation
C(O[C:4]([C:6]1[N:7]=[C:8]([C:15]2[C:20]([F:21])=[CH:19][CH:18]=[CH:17][C:16]=2[F:22])[N:9]([CH3:14])[C:10](=[O:13])[C:11]=1[OH:12])=[O:5])C.[Cl:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28][NH2:29])=[CH:26][CH:25]=1>>[Cl:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28][NH:29][C:4]([C:6]2[N:7]=[C:8]([C:15]3[C:16]([F:22])=[CH:17][CH:18]=[CH:19][C:20]=3[F:21])[N:9]([CH3:14])[C:10](=[O:13])[C:11]=2[OH:12])=[O:5])=[CH:26][CH:25]=1

Participants

3

Reactant 2

HCID 660364-ChlorobenzylamineHCID 546914342-(2,6-Difluoro-phenyl)-5-hydroxy-1-methyl-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid ethyl ester

Product 1

HCID 54705249N-(4-chlorobenzyl)-2-(2,6-difluorophenyl)-5-hydroxy-1-methyl-6-oxo-1,6-dihydropyrimidine-4-carboxamide

Procedure

Prepared according to the procedure described for example 2 from 2-(2,6-difluoro-phenyl)-5-hydroxy-1-methyl-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid ethyl ester (31 mg, 0.1 mmol) and 4-chlorobenzylamine (71 mg, 0.5 mmol). The title product was obtained as an off-white solid (32.3 mg, 80% yield). 1HNMR (500 MHz, CDCl3) δ: 12.25 (1H, s), 7.80 (1H, br s), 7.52–7.46 (1H, m), 7.81 (2H, d, J=8.55 Hz), 7.25 (2H, d, J=8.24 Hz), 7.05 (2H, dd, J=8.54, 7.32 Hz), 4.55 (2H, d, J=6.10 Hz), 3.41 (3H, s). HRMS (ESI) calcd for C19H15ClF2N3O3 (M+H): 406.0770; found: 406.0775.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-85dad78e832643c9ab8733f493241b95
Source dataset
uspto-grants-2006_05
Patent number
US07037908B2

Reaction notes

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