2,4-Difluorobenzylamine → N-(2,4-difluorobenzyl)-2-(2,6-difluorophenyl)-5-hydroxy-1-methyl-6-oxo-1,6-dihydropyrimidine-4-carboxamide
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:31]=[C:30]([F:32])[CH:29]=[CH:28][C:25]=1[CH2:26][NH2:27]>>[F:23][C:24]1[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:25]=1[CH2:26][NH:27][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
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 2,4-difluorobenzylamine (72 mg, 0.5 mmol). The title product was obtained as an off-white solid (36.2 mg, 89% yield). 1HNMR (500 MHz, CDCl3) δ: 12.13 (1H, s), 7.87 (1H, br s), 7.06 (2H, dd, J=8.54, 7.33 Hz), 6.86–6.81 (2H, m), 6.75–6.69 (2H, m), 4.56 (2H, d, J=6.41 Hz), 3.42 (3H, s). HRMS (ESI) calcd for C19H12F4N3O3 (M−H): 406.0815; found: 406.0812.
Workup
- customPrepared
Sources & evidence
- ORD record
- ord-059e4d255cb2422a9bc1039bcc10d92c
- Source dataset
- uspto-grants-2006_05
- Patent number
- US07037908B2
Reaction notes
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