Water → 6-methyl-4-phenoxy-5H-pyrrolo[3,2-d]pyrimidine

HRID 1787028Notes

Reaction equation

[O:1]([C:8]1[C:13]([NH2:14])=[C:12]([C:15]#[C:16][CH3:17])[N:11]=[CH:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].O>O1CCCC1>[CH3:17][C:16]1[NH:14][C:13]2[C:8]([O:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[N:9][CH:10]=[N:11][C:12]=2[CH:15]=1

Participants

Conditions

Temperature: 0 °C

Procedure

4-Phenoxy-6-prop-1-yn-1-ylpyrimidin-5-amine (776.0 mg) was dissolved in tetrahydrofuran (30 mL) and cooled to 0° C. To this solution was added dropwise a 1.0 M solution (4 mL) of potassium tert-butoxide in tetrahydrofuran, and the mixture was stirred at room temperature for 30 min. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was separated and purified by silica gel column chromatography (eluent, hexane:ethyl acetate=67:33→20:80) to give the title compound (578.6 mg) as a white solid.

Workup

extractionthe mixture was extracted with ethyl acetate
washThe organic layer washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was separated
custompurified by silica gel column chromatography (eluent, hexane:ethyl acetate=67:33→20:80)

Sources & evidence

ORD record: ord-761d2778fbd049bab6f85c1e6557ac82
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07507740B2

Reaction notes

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