1-Phenethylamine → HCID 54711733, compound

HRID 1822694Notes

Reaction equation

HRID 1822694 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.[CH3:23][CH:24]([NH2:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>>[F:21][C:20]1[CH:19]=[CH:18][CH:17]=[C:16]([F:22])[C:15]=1[C:8]1[N:9]([CH3:14])[C:10](=[O:13])[C:11]([OH:12])=[C:6]([C:4]([NH:31][CH:24]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH3:23])=[O:5])[N:7]=1

Participants

3

Reactant 2

HCID 74081-PhenethylamineHCID 546914342-(2,6-Difluoro-phenyl)-5-hydroxy-1-methyl-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid ethyl ester

Product 1

HCID 54711733HCID 54711733, compound

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 α-methylbenzylamine (61 mg, 0.5 mmol). The title product was obtained as an off-white solid (24.6 mg, 64% yield). 1HNMR (500 MHz, CDCl3) δ: 12.39 (1H, s), 7.71 (1H, d, J=7.94 Hz), 7.54–7.48 (1H, m), 7.36–7.25 (5H, m), 7.06 (2H, dd, J=14.65, 8.54 Hz), 5.22 (1H, qt, J=7.02 Hz), 3.40 (3H, s), 1.58 (3H, d, J=7.02 Hz). HRMS (ESI) calcd for C20H16F2N3O3 (M−H): 384.1160; found: 384.1161.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-779886ff4c1242178ffc3989b1938b70
Source dataset
uspto-grants-2006_05
Patent number
US07037908B2

Reaction notes

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