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

HRID 28232Notes

Reaction equation

HRID 28232 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-9c538c8c20f146a788e137975b1421d1
Source dataset
uspto-grants-1980_09
Patent number
US04225710

Reaction notes

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