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

HRID 1926115Notes

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 was 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 was 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-9ef2866dab4842379359b9a7c29f4472
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08178543B2

Reaction notes

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