Benzenemethanamine, 3,4-dichloro- → N-(3,4-dichlorobenzyl)-5-hydroxy-2-(2-methoxyphenyl)-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[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.[Cl:23][C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][C:31]=1[Cl:32])[CH2:27][NH2:28]>>[Cl:23][C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][C:31]=1[Cl:32])[CH2:27][NH:28][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]Participants
3
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 3,4-dichlorobenzylamine (132 mg, 0.75 mmol). The title product was obtained as a pink solid (55.5 mg, 85% yield). 1HNMR (500 MHz, CDCl3) δ: 11.98 (1H, s), 7.95 (1H, t, J=5.19 Hz), 7.49 (1H, td, J=7.33, 1.83 Hz),7.40–7.38 (2H, m), 7.29 (1H, dd, J=7.63, 1.83 Hz), 7.15 (1H, dd, J=8.24, 1.83 Hz), 7.07 (1H, t, J=8.24 Hz), 4.51 (2H, d, J=6.41 Hz), 3.82 (3H, s), 3.35 (3H, s). HRMS (ESI) calcd for C20H18Cl2N3O4 (M+H): 434.0675; found: 434.0674.
Workup
- customPrepared
Sources & evidence
- ORD record
- ord-161822cec23d4f4488c1673949f67d7b
- Source dataset
- uspto-grants-2006_05
- Patent number
- US07037908B2
Reaction notes
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