2-Aminothiophenol → 6-Amino-5-[(2-aminophenyl)sulfanyl]pyrimidine-2,4(1H,3H)-dione

HRID 1981932Notes

Reaction equation

HRID 1981932 reaction equation
[NH2:1][C:2]1[NH:7][C:6](=[O:8])[NH:5][C:4](=[O:9])[C:3]=1Br.C(=O)([O-])[O-].[K+].[K+].[NH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[SH:24]>C(O)CO>[NH2:1][C:2]1[NH:7][C:6](=[O:8])[NH:5][C:4](=[O:9])[C:3]=1[S:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[NH2:17]

Participants

5

Reactant 3

HCID 87132-AminothiophenolHCID 11430Potassium CarbonateHCID 805786-Amino-5-bromouracil

Product 1

HCID 201894366-Amino-5-[(2-aminophenyl)sulfanyl]pyrimidine-2,4(1H,3H)-dioneYield 32%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

10.3 g of 6-amino-5-bromo-2,4(1H,3H)-pyrimidinedione, 7.0 g of potassium carbonate and 9.0 g of 2-aminothiophenol in 150 ml of ethylene glycol are heated at 170° C. under a nitrogen atmosphere for 4 hours. After filtration, the reaction mixture is poured onto 400 ml of water and decanted from the oily residue. After acidification with acetic acid, 4 g of 6-amino-5-(2-amino-phenylthio)-2,4(1H,3H)-pyrimidinedione are obtained, and are purified by recrystallization from ethanol/water.

Workup

  1. filtrationAfter filtration
  2. additionthe reaction mixture is poured onto 400 ml of water
  3. customdecanted from the oily residue

Sources & evidence

ORD record
ord-7600e8cc0f104033a469706a8fa566ba
Source dataset
uspto-grants-1986_06
Patent number
US04594419

Reaction notes

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