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 absoulute 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-2da7edcef5024c9eaa39f1a89d35c165
Source dataset: uspto-grants-1977_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04053474

Reaction notes

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