Water → 4-Amino-5-(2-methoxy-4-methylmercapto-benzoylamino)-pyrimidin-2,6-dione

HRID 3861Notes

Reaction equation

HRID 3861 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]([S:12][CH3:13])[CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=O.[NH2:14][C:15]1[NH:16][C:17](=[O:23])[NH:18][C:19](=[O:22])[C:20]=1[NH2:21].O>CN(C)C=O>[NH2:14][C:15]1[NH:16][C:17](=[O:23])[NH:18][C:19](=[O:22])[C:20]=1[NH:21][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][C:10]([S:12][CH3:13])=[CH:11][C:3]=1[O:2][CH3:1]

Participants

5

Reactant 3

HCID 962WaterHCID 767265,6-DiaminouracilHCID 6433294-(Methylthio)-o-anisic acid

Product 1

HCID 135324034-Amino-5-(2-methoxy-4-methylmercapto-benzoylamino)-pyrimidin-2,6-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Twenty grams of 2-methoxy-4-methylmercapto-benzoic acid is dissolved in 260 ml of dimethylformamide, mixed with 13 gm of N,N'-carbonyl-diimidazole, and stirred for 30 minutes at ambient temperature. Then, 13 gm of 4,5-diamino-pyrimidin-2,6-dione are added, and the reaction mixture is refluxed for three hours with stirring. After cooling, it is poured into 1 liter of water. The product precipitated is suction filtered, washed with water, and dried at 70° C. in a circulating air drier.

Workup

  1. temperaturethe reaction mixture is refluxed for three hours
  2. stirringwith stirring
  3. temperatureAfter cooling
  4. customThe product precipitated
  5. filtrationfiltered
  6. washwashed with water
  7. customdried at 70° C. in a circulating air drier

Sources & evidence

ORD record
ord-bb53e3adbf81433d844364e852ee7c9c
Source dataset
uspto-grants-1988_02
Patent number
US04722929

Reaction notes

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