Sodium borohydride → 4-[2-Hydroxy-1,1-dimethyl-3-(4-pyrimidinyl)propoxy]benzonitrile

HRID 1073953Notes

Reaction equation

[BH4-].[Na+].[OH:3][C:4](=[CH:17][C:18]1[CH:23]=[CH:22][N:21]=[CH:20][N:19]=1)[C:5]([CH3:16])([CH3:15])[O:6][C:7]1[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][CH:8]=1>C(O)C>[OH:3][CH:4]([CH2:17][C:18]1[CH:23]=[CH:22][N:21]=[CH:20][N:19]=1)[C:5]([CH3:15])([CH3:16])[O:6][C:7]1[CH:8]=[CH:9][C:10]([C:11]#[N:12])=[CH:13][CH:14]=1

Participants

Conditions

Temperature: 20 °C

Procedure

0.013 mg of sodium borohydride was added to a solution of 0.098 mg of 4-[2-hydroxy-1,1-dimethyl-3-(4-pyrimidinyl)-2-propenyloxy]benzonitrile in 3 ml of ethanol and the solution was stirred at 20° C. for 16 hours. The solvent was removed by evaporation and the residue was partitioned between ethyl acetate and water. The organic phase was evaporated and the residue was chromatographed on silica gel using ethyl acetate for the elution. There was obtained 0.073 g of 4-[2-hydroxy-1,1-dimethyl-3-(4-pyrimidinyl)propoxy]benzonitrile in the form of a white solid of melting point 96°-98° C.

Workup

customThe solvent was removed by evaporation
customthe residue was partitioned between ethyl acetate and water
customThe organic phase was evaporated
customthe residue was chromatographed on silica gel
washfor the elution

Sources & evidence

ORD record: ord-043738df25ec4b82aaf4257a235dcd73
Source dataset: uspto-grants-1990_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04971982

Reaction notes

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