3,4-Difluorobenzylamine → N-(3,4-difluorobenzyl)-2-(2,6-difluorophenyl)-5-hydroxy-1-methyl-6-oxo-1,6-dihydropyrimidine-4-carboxamide

HRID 1822684Notes

Reaction equation

HRID 1822684 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.[F:23][C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][C:31]=1[F:32])[CH2:27][NH2:28]>>[F:23][C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][C:31]=1[F:32])[CH2:27][NH:28][C:4]([C:6]1[N:7]=[C:8]([C:15]2[C:16]([F:22])=[CH:17][CH:18]=[CH:19][C:20]=2[F:21])[N:9]([CH3:14])[C:10](=[O:13])[C:11]=1[OH:12])=[O:5]

Participants

3

Reactant 2

HCID 1235723,4-DifluorobenzylamineHCID 546914342-(2,6-Difluoro-phenyl)-5-hydroxy-1-methyl-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid ethyl ester

Product 1

HCID 54711131N-(3,4-difluorobenzyl)-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-dihydropyrimidine-4-carboxylic acid ethyl ester (31 mg, 0.1 mmol) and 3,4-difluorobenzylamine (72 mg, 0.5 mmol). The title product was obtained as an off-white solid (32.7 mg, 80% yield). 1HNMR (500 MHz, CDCl3) δ: 12.18 (1H, s), 7.83 (1H, br s), 7.53–7.47 (1H, m), 7.15–7.02 (5H, m), 4.53 (2H, d, J=6.41 Hz), 3.41 (3H, s). HRMS (ESI) calcd for C19H14F4N3O3 (M+H): 408.0971; found: 408.0969.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-008a04d454f1498bb2057dff704e055e
Source dataset
uspto-grants-2006_05
Patent number
US07037908B2

Reaction notes

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