4-Fluorobenzylamine → N-(4-fluorobenzyl)-5-hydroxy-2-(2-methoxyphenyl)-1-methyl-6-oxo-1,6-dihydropyrimidine-4-carboxamide

HRID 1822702Notes

Reaction equation

HRID 1822702 reaction equation
C(O[C:4]([C:6]1[N:7]=[C:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[O:21][CH3:22])[N:9]([CH3:14])[C:10](=[O:13])[C:11]=1[OH:12])=[O:5])C.[F:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28][NH2:29])=[CH:26][CH:25]=1>>[F: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[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[O:21][CH3:22])[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 673264-FluorobenzylamineHCID 546914385-Hydroxy-2-(2-methoxy-phenyl)-1-methyl-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid ethyl ester

Product 1

HCID 54711755N-(4-fluorobenzyl)-5-hydroxy-2-(2-methoxyphenyl)-1-methyl-6-oxo-1,6-dihydropyrimidine-4-carboxamide

Procedure

Prepared according to the procedure described for example 2 from 5-hydroxy-2-(2-methoxy-phenyl)-1-methyl-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid ethyl ester (45.6 mg, 0.15 mmol) and 4-fluorobenzylamine (95 mg, 0.75 mmol). The title product was obtained as a pink solid (37 mg, 64% yield). 1HNMR (500 MHz, CDCl3) δ: 12.13 (1H, s), 7.90 (1H, t, J=5.50 Hz), 7.48 (1H, td, J=7.02, 1.83 Hz), 7.29–7.26 (3H, m), 7.06 (1H, t, J=7.33 Hz), 7.02–6.97 (3H, m),4.53 (2H, d, J=6.41 Hz), 3.81 (3H, s), 3.34 (3H, s). HRMS (ESI) calcd for C20H19FN3O4 (M+H): 384.1360; found: 384.1370.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-0e01351c38e7455daa08f566706b9bce
Source dataset
uspto-grants-2006_05
Patent number
US07037908B2

Reaction notes

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