Sodium Sulfate → 4-(4-Fluorophenyl)-2,6-dimethyl-5-pyrimidinemethanol

HRID 1607896Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14](OCC)=[O:15])=[C:12]([CH3:19])[N:11]=[C:10]([CH3:20])[N:9]=2)=[CH:4][CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C.S([O-])([O-])(=O)=O.[Na+].[Na+]>ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:13]([CH2:14][OH:15])=[C:12]([CH3:19])[N:11]=[C:10]([CH3:20])[N:9]=2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 46.5 g (0.169 mol) of ethyl 4-(4-fluorophenyl)-2,6-dimethyl-5-pyrimidinecarboxylate in 500 mL of dichloromethane at -78° C. under nitrogen was added 340 mL of a 1M solution of diisobutylaluminum hydride (0.339 mol) in dichloromethane. Theresulting mixture was stirred at -78° C. for one-half hour and then the reaction was quenched by the addition of a saturated aqueous solution of sodium sulfate (48.15 g, 0.34 mol). The cooling bath was removed and the mixture was vigorously stirred for twenty minutes and then filtered through Celite®. The filter cake was thoroughly washed with chloroformand the combined filtrate and washings were dried over anhydrous magnesium sulfate and evaporated to yield 31.14 g of 4-(4-fluorophenyl)-2,6-dimethyl-5-pyrimidinemethanol, mp 174°-176° C.

Workup

customThe cooling bath was removed
stirringthe mixture was vigorously stirred for twenty minutes
filtrationfiltered through Celite®
washThe filter cake was thoroughly washed with chloroformand the combined filtrate and washings
dry with materialwere dried over anhydrous magnesium sulfate
customevaporated

Sources & evidence

ORD record: ord-23f18d898e394dab94f1fda0c3702136
Source dataset: uspto-grants-1989_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04868185

Reaction notes

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