Methyl pyruvate → 5,7-diamino-1,3-dimethylpyrimido(4,5-c)pyridazin-4(1H)-one

HRID 1155563Notes

Reaction equation

HRID 1155563 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[C:4]([N:9]([CH3:11])[NH2:10])[N:3]=1.[C:12](OC)(=[O:16])[C:13]([CH3:15])=O>CO>[NH2:8][C:6]1[C:5]2[C:12](=[O:16])[C:13]([CH3:15])=[N:10][N:9]([CH3:11])[C:4]=2[N:3]=[C:2]([NH2:1])[N:7]=1

Participants

4

Reactant 2

HCID 11748Methyl pyruvateHCID 124630642,4-Diamino-6-(1-methylhydrazino)pyrimidine

Product 1

HCID 124630735,7-diamino-1,3-dimethylpyrimido(4,5-c)pyridazin-4(1H)-oneYield 76%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a refluxing solution of 2,4-diamino-6-(1-methylhydrazino)pyrimidine (500 mg) in anhydrous methanol (15 ml) was added methyl pyruvate (496 mg) over a five minute period. Reflux was continued for 5 hours after which time the solid which had separated was collected by suction filtration of the hot mixture, washed with methanol, and dried under vacuum at 70° C. to yield tan crystals of 5,7-diamino-1,3-dimethylpyrimido(4,5-c)-pyridazine-4(1H)-one (508 mg; 76% of theoretical yield; m.p. >275° C.).

Workup

  1. temperatureReflux
  2. customafter which time the solid which had separated
  3. filtrationwas collected by suction filtration of the hot mixture
  4. washwashed with methanol
  5. customdried under vacuum at 70° C.

Sources & evidence

ORD record
ord-7bcde3e3ce6d42108fe77152f282d7e6
Source dataset
uspto-grants-1981_11
Patent number
US04302587

Reaction notes

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