Hydrazine hydrate (1:1) → 5-Cyano-2-hydrazino-4-methylamino-pyrimidine

HRID 53618Notes

Reaction equation

HRID 53618 reaction equation
[C:1]([C:3]1[C:4]([NH:11][CH3:12])=[N:5][C:6](C)=[N:7][C:8]=1S)#[N:2].O.[NH2:14][NH2:15]>C(O)C>[C:1]([C:3]1[C:4]([NH:11][CH3:12])=[N:5][C:6]([NH:14][NH2:15])=[N:7][CH:8]=1)#[N:2]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 178482389HCID 178482389, compound

Product 1

HCID 218527585-Cyano-2-hydrazino-4-methylamino-pyrimidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-cyano-4-methylamino-2-methyl-sulfanyl-pyrimidine (25.86 g) from Example 3 and hydrazine hydrate (52 mL) in ethanol (250 mL) was heated at reflux with stirring for 3 hours. The reaction mixture was cooled to room temperature and the insoluble product was collected by filtration, washed with cold aqueous ethanol (1:1) to give 23 g of the title compound. Crystallization from ethanol afforded an analytically pure sample of 5-cyano-2-hydrazino-4-methylamino-pyrimidine, mp 247°-249° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. filtrationthe insoluble product was collected by filtration
  4. washwashed with cold aqueous ethanol (1:1)

Sources & evidence

ORD record
ord-32a7079ccd93419e8ce51720f23e7430
Source dataset
uspto-grants-1997_04
Patent number
US05620981

Reaction notes

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