Benzo-1,3-dioxole-5-methylamine → N-(benzo[d][1,3]dioxol-5-ylmethyl)-2-(2,6-difluorophenyl)-5-hydroxy-1-methyl-6-oxo-1,6-dihydropyrimidine-4-carboxamide

HRID 1822693Notes

Reaction equation

HRID 1822693 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.[CH2:23]([NH2:33])[C:24]1[CH:32]=[CH:31][C:30]2[O:29][CH2:28][O:27][C:26]=2[CH:25]=1>>[O:29]1[C:30]2[CH:31]=[CH:32][C:24]([CH2:23][NH:33][C:4]([C:6]3[N:7]=[C:8]([C:15]4[C:16]([F:22])=[CH:17][CH:18]=[CH:19][C:20]=4[F:21])[N:9]([CH3:14])[C:10](=[O:13])[C:11]=3[OH:12])=[O:5])=[CH:25][C:26]=2[O:27][CH2:28]1

Participants

3

Reactant 2

HCID 75799Benzo-1,3-dioxole-5-methylamineHCID 546914342-(2,6-Difluoro-phenyl)-5-hydroxy-1-methyl-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid ethyl ester

Product 1

HCID 54687117N-(benzo[d][1,3]dioxol-5-ylmethyl)-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 piperonylamine (76 mg, 0.5 mmol). The title product was obtained as an off-white solid (18.6 mg, 45% yield). 1HNMR (500 MHz, CDCl3) δ: 12.35 (1H, s), 7.74 (1H, br s), 7.52–7.46 (1H, m), 7.04 (2H, dd, J=8.24, 7.33 Hz), 6.80 (1H, s), 6.78–6.74 (2H, m), 5.93 (2H, s), 4.48 (2H, d, J=6.10 Hz), 3.40 (3H, s). HRMS (ESI) calcd for C20H14F2N3O5 (M−H): 414.0902; found: 414.0900.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-30566104f4ae4363bb79d23462592953
Source dataset
uspto-grants-2006_05
Patent number
US07037908B2

Reaction notes

Loading…