Methylhydrazine → 2,4-Diamino-6-(1-methylhydrazino)pyrimidine

HRID 127189Notes

Reaction equation

HRID 127189 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH2:8])[N:5]=[C:4]([NH2:9])[CH:3]=1.[CH3:10][NH:11][NH2:12]>CO>[NH2:8][C:6]1[N:5]=[C:4]([NH2:9])[CH:3]=[C:2]([N:11]([CH3:10])[NH2:12])[N:7]=1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 674322,4-Diamino-6-chloropyrimidine

Product 1

HCID 124630642,4-Diamino-6-(1-methylhydrazino)pyrimidineYield 56%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a refluxing solution of 6-chloro-2,4-diaminopyrimidine (4.0 g) in anhydrous methanol (40 ml) was added methylhydrazine (3.2 g). After 18 hours the refluxing mixture was allowed to cool to room temperature under a nitrogen atmosphere in order that the product could crystallise out. The white solid (3.0 g) was collected by filtration and dried under reduced pressure at 70° C. Recrystallisation of the product from methanol/methylhydrazine (50/l) gave straw-coloured crystals of 2,4-diamino-6-(1-methylhydrazino)pyrimidine (1.92 g; 56% of theoretical yield; M.P. 214°-217° C. decomposition).

Workup

  1. customcould crystallise out
  2. filtrationThe white solid (3.0 g) was collected by filtration
  3. customdried under reduced pressure at 70° C
  4. customRecrystallisation of the product from methanol/methylhydrazine (50/l)

Sources & evidence

ORD record
ord-316f168b166d4fa3aaad4f3bb9549663
Source dataset
uspto-grants-1981_03
Patent number
US04255427

Reaction notes

Loading…