Water → 3-(2-Pyrimidinyloxy)-benzaldehyde dimethyl acetal

HRID 1740442Notes

Reaction equation

[CH3:1][O:2][CH:3]([O:11][CH3:12])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([OH:10])[CH:5]=1.CC(C)([O-])C.[K+].Cl[C:20]1[N:25]=[CH:24][CH:23]=[CH:22][N:21]=1.O>CN(C)C=O>[CH3:1][O:2][CH:3]([O:11][CH3:12])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][C:20]2[N:25]=[CH:24][CH:23]=[CH:22][N:21]=2)[CH:5]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 168 mg of 3-hydroxybenzaldehyde dimethyl acetal in 2 ml of anhydrous dimethylformamide was stirred under nitrogen and 220 mg of potassium tert.butoxide were added. The mixture was heated at 60° C. for 1 hour, then cooled to room temperature and 114 mg of 2-chloropyrimidine were added in portions. The mixture was heated at 150° C. for 20 hours. After cooling 20 ml of water were added and the product was extracted with ethyl acetate. The extracts were washed with 10 ml of 1M sodium hydroxide solution and 5 ml of brine and then dried over anhydrous magnesium sulphate. After filtration and evaporation of the filtrate the residual brown gum was purified by column chromatography on silica gel using ethyl acetate/hexane (1:1) for the elution to give 3-(2-pyrimidinyloxy)-benzaldehyde dimethyl acetal as a syrup.

Workup

temperaturecooled to room temperature
temperatureThe mixture was heated at 150° C. for 20 hours
additionwere added
extractionthe product was extracted with ethyl acetate
washThe extracts were washed with 10 ml of 1M sodium hydroxide solution and 5 ml of brine
dry with materialdried over anhydrous magnesium sulphate
filtrationAfter filtration and evaporation of the filtrate the residual brown gum
customwas purified by column chromatography on silica gel
washfor the elution

Sources & evidence

ORD record: ord-22e4f265ca6249b79a9147b473a8377d
Source dataset: uspto-grants-1999_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05969139

Reaction notes

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