m-Chloroperbenzoic acid → 6-[3-(4-Cyanophenoxy)-2-hydroxy-3-methylbutyl]pyrimidine 1-oxide

HRID 1073954Notes

Reaction equation

ClC1C=CC=C(C(OO)=[O:9])C=1.[OH:12][CH:13]([CH2:26][C:27]1[CH:32]=[CH:31][N:30]=[CH:29][N:28]=1)[C:14]([CH3:25])([CH3:24])[O:15][C:16]1[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=1>ClCCl>[C:20]([C:19]1[CH:18]=[CH:17][C:16]([O:15][C:14]([CH3:24])([CH3:25])[CH:13]([OH:12])[CH2:26][C:27]2[N+:28]([O-:9])=[CH:29][N:30]=[CH:31][CH:32]=2)=[CH:23][CH:22]=1)#[N:21]

Participants

Conditions

Temperature: 20 °C

Procedure

3.77 g of m-chloroperbenzoic acid were added to a solution of 4.78 g of 4-[2-hydroxy-1,1-dimethyl-3-(4pyrimidinyl)propoxy]benzonitrile in 75 ml of dichloromethane and the mixture was stirred at 20° C. for 16 hours. A further 0.38 g of m-chloroperbenzoic acid was added and the mixture was stirred at 20° C. for 24 hours. The mixture was then washed in succession with water and sodium chloride solution. The organic solution was evaporated and the residue was chromatographed on silica gel using diethyl ether/methanol (9:1) for the elution to give 0.98 g of 6-[3-(4-cyanophenoxy)-2-hydroxy-3-methylbutyl]pyrimidine 1-oxide in the form of a white solid of melting point 105°-107.5° C. (from ethyl acetate).

Workup

stirringthe mixture was stirred at 20° C. for 24 hours
washThe mixture was then washed in succession with water and sodium chloride solution
customThe organic solution was evaporated
customthe residue was chromatographed on silica gel
washfor the elution

Sources & evidence

ORD record: ord-3300d1647c0a4d34a9ac5cc3d1c4f59f
Source dataset: uspto-grants-1990_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04971982

Reaction notes

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