Sodium hydride → HCID 57086818, compound

HRID 1977616Notes

Reaction equation

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

Participants

Conditions

Temperature: 25 °C

Procedure

With cooling, 0.4 g (0.01 mol) of sodium hydride (60%) are added to a mixture of 2 g (0.0096 mol) of 2-(2-hydroxy-phenyl)-2-methoxyimino-N-methyl-acetamide and 2.3 g (0.0095 mol) of 4-(2-chlorophenoxy)-5,6-difluoropyrimidine in 10 ml of dimethylformamide, and the mixture is stirred at 25° C. for 12 hours. The reaction mixture is poured onto water and extracted with dichloromethane, the organic phase is dried over sodium sulphate and the solvent is distilled off under reduced pressure. The residue is chromatographed over silica gel using a mixture of identical volumina of ethyl acetate and cyclohexane. 2.1 g (48.3% of theory) of 2-{2-[6-(2-chlorophenoxy)-5-fluoro-pyrimidine-4-yloxy]-phenyl}-2-methoxyimino-N-methylacetamide are obtained.

Workup

temperatureWith cooling
additionThe reaction mixture is poured onto water
extractionextracted with dichloromethane
dry with materialthe organic phase is dried over sodium sulphate
distillationthe solvent is distilled off under reduced pressure
customThe residue is chromatographed over silica gel using
additiona mixture of identical volumina of ethyl acetate and cyclohexane

Sources & evidence

ORD record: ord-007300ba94f04676a6aba2de55604e84
Source dataset: uspto-grants-2001_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06235743B1

Reaction notes

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