Ethanol → 4-Hydrazinyl-1-methyl-1H-pyrazolo[3,4-d]pyrimidine

Reaction equation

Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]2[NH:8][N:9]=[CH:10][C:3]=12.O.[NH2:12][NH2:13].[CH2:14](O)C>>[NH:12]([C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH3:14])[N:9]=[CH:10][C:3]=12)[NH2:13]

Participants

Reactant 3

HCID 702Ethanol2×

HCID 24654Hydrazine hydrate (1:1)

HCID 2210954-Chloro-1H-pyrazolo[3,4-d]pyrimidine

Product 1

HCID 2197854-Hydrazinyl-1-methyl-1H-pyrazolo[3,4-d]pyrimidine

Procedure

50 g. of 4-chloropyrazolo[3,4-d]pyrimidine are dissolved in 700 ml. of absolute ethanol and 25 g. of hydrazine hydrate in 100 ml. of ethanol are slowly added dropwise with stirring. This is stirred for 13 hours at room temperature and the product formed is then filtered under suction, water is added and the product, 4-hydrazino-1-methylpyrazolo[3,4-d]pyrimidine, is crystallized from dimethylformamide as yellowish crystals, m.p. 231°.

Workup

stirringThis is stirred for 13 hours at room temperature
customthe product formed
filtrationis then filtered under suction, water
additionis added
customthe product, 4-hydrazino-1-methylpyrazolo[3,4-d]pyrimidine, is crystallized from dimethylformamide as yellowish crystals, m.p. 231°

Sources & evidence

ORD record: ord-a270fd47da1e47c0978cfde1f3230638
Source dataset: uspto-grants-1978_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04087423

Reaction notes

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