Hydrochloric Acid → 3-{2-Chloro-4-fluoro-5-[2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}-2-(methoxycarbonyl)methoxypyridine

HRID 1862339Notes

Reaction equation

[H-].[Na+].[NH2:3]/[C:4](/[C:11]([F:14])([F:13])[F:12])=[CH:5]\[C:6]([O:8]CC)=O.[Cl:15][C:16]1[C:21]([O:22][C:23]2[C:24]([O:29][CH2:30][C:31]([O:33][CH3:34])=[O:32])=[N:25][CH:26]=[CH:27][CH:28]=2)=[CH:20][C:19]([N:35]=[C:36]=[O:37])=[C:18]([F:38])[CH:17]=1.Cl>CN(C)C=O>[Cl:15][C:16]1[CH:17]=[C:18]([F:38])[C:19]([N:35]2[C:6](=[O:8])[CH:5]=[C:4]([C:11]([F:12])([F:13])[F:14])[NH:3][C:36]2=[O:37])=[CH:20][C:21]=1[O:22][C:23]1[C:24]([O:29][CH2:30][C:31]([O:33][CH3:34])=[O:32])=[N:25][CH:26]=[CH:27][CH:28]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a mixture of 1 ml of N,N-dimethylformamide and 26 mg of sodium hydride, a solution of 126 mg of ethyl 3-amino-4,4,4-trifluorocrotonate in 1 ml of N,N-dimethylformamide was added and the mixture was stirred at 0° C. Thereafter, to the reaction mixture was added a mixture of 266 mg of 4-chloro-2-fluoro-5-{2-(methoxycarbonyl)methoxy-3-pyridyloxy}phenyl isocyanate and 1 ml of N,N-dimethylformamide at the same temperature, and the mixture was stirred over night at room temperature. The reaction solution was poured into a mixture of hydrochloric acid and ice water, and to obtain 3-{2-chloro-4-fluoro-5-[2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}-2-(methoxycarbonyl)methoxypyridine.

Workup

additionThereafter, to the reaction mixture was added
stirringthe mixture was stirred over night at room temperature

Sources & evidence

ORD record: ord-6732037b723c423f8924de54a13ed7d3
Source dataset: uspto-grants-2003_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06537948B1

Reaction notes

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