Hydrazine → HCID 178492932, compound

Participants

Reaction Steps

2-((3-fluoro-5-methoxyphenyl)(methoxy)methylene)malononitrile (BA69, 0.029 mol) stirred in EtOH (20 ml) at room temperature under an argon atmosphere. Hydrazine (1.4 ml, 29 mmol) was added and reaction was left stirring for 90 minutes. Reaction mixture was concentrated in vacuo and dried on vacuum pump overnight to yield intermediate 5-amino-3-(3-fluoro-5-methoxyphenyl)-1H-pyrazole-4-carbonitrile (BA73). Formamide (20 ml) was added and reaction was heated to 180° C. under an argon atmosphere overnight. Reaction was cooled and dH2O was added (40 ml) forcing a white precipitate out of solution. Precipitate was collected and washed with dH2O. Solid was dried and purified by silica gel column chromatography [MeOH—CH2Cl2, 10:90] to yield 3-(3-fluoro-5-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (BA75).

Provenance & Evidence