Formamide → 5-Amino-1,3-dimethylpyrimido[4,5-d]pyrimidine-2,4(1H,3H)-dione

HRID 476913Notes

Reaction equation

HRID 476913 reaction equation
[NH2:1][C:2]1[N:7]([CH3:8])[C:6](=[O:9])[N:5]([CH3:10])[C:4](=[O:11])[C:3]=1[C:12]#[N:13].[CH:14]([NH2:16])=O>O>[NH2:13][C:12]1[N:16]=[CH:14][N:1]=[C:2]2[N:7]([CH3:8])[C:6](=[O:9])[N:5]([CH3:10])[C:4](=[O:11])[C:3]=12

Participants

4

Reactant 2

HCID 713FormamideHCID 13296989HCID 13296989, compound

Product 1

HCID 124906845-Amino-1,3-dimethylpyrimido[4,5-d]pyrimidine-2,4(1H,3H)-dioneYield 58%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.3 g (1.7 mmol) of 6-amino-5-cyano-1,3-dimethyluracil was added to 2 ml of formamide followed by refluxing for 2 hours. 10 ml of water was added to the solution and the crystalline precipitate was filtered off. The crude product was recrystallized from methanol to give 0.2 g of 5-amino-1,3-dimethylpyrimido[4,5-d]pyrimidine-2,4-dione (compound 9) in a 58% yield.

Workup

  1. temperatureby refluxing for 2 hours
  2. filtrationthe crystalline precipitate was filtered off
  3. customThe crude product was recrystallized from methanol

Sources & evidence

ORD record
ord-378c039ac0b149548c2c17594842b502
Source dataset
uspto-grants-1989_12
Patent number
US04886807

Reaction notes

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