Hydrazine → 4-Chloro-6-hydrazinyl-2-(methylsulfanyl)pyrimidine

HRID 2389764

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6](Cl)[N:5]=[C:4]([S:9][CH3:10])[N:3]=1.[NH2:11][NH2:12]>C1COCC1>[Cl:1][C:2]1[CH:7]=[C:6]([NH:11][NH2:12])[N:5]=[C:4]([S:9][CH3:10])[N:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

33 g (169.2 mmol) of 4,6-dichloro-2-(methylthio)pyrimidine are introduced into 300 ml of THF at −20° C., and 169 ml of a 1M solution of hydrazine in THF is added dropwise at a rate such that the temperature does not rise above −15° C. The mixture is stirred at 0° C. for a further 2 h. After the reaction is complete, the solvent is distilled off and the residue is stirred with diethyl ether. 18.4 g (57% of theory) of the product are obtained as a solid.

Workup

customdoes not rise above −15° C
distillationthe solvent is distilled off
stirringthe residue is stirred with diethyl ether
custom18.4 g (57% of theory) of the product are obtained as a solid

Sources & evidence

ORD record: ord-5eaf8aeddcf1430d8ea9d2394de1b059
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08273752B2

Linked notes

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