Acetic Acid → 6-Chloro-2,3-dihydro-3-hydroxy-2-imino-4-pyrimidinamine

HRID 868637Notes

Reaction equation

HRID 868637 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4]([NH2:9])[N:3]=1.C(O)(=[O:12])C.OO>O1CCCC1>[NH2:9][C:4]1[N:3]([OH:12])[C:2](=[NH:1])[N:7]=[C:6]([Cl:8])[CH:5]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 674322,4-Diamino-6-chloropyrimidine

Product 1

HCID 15515256-Chloro-2,3-dihydro-3-hydroxy-2-imino-4-pyrimidinamineYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.5 g (10 mmoles) of 2,6-diamino-4-chloropyrimidine are dissolved in 20 ml of anhydrous tetrahydrofuran. A mixture of 10 ml of acetic acid and 2 ml of a 70% aqueous hydrogen peroxide solution is added in 30 minutes under stirring and reflux. The reaction mixture is boiled for four hours, evaporated in vacuo to third of its volume, and a 40% aqueous sodium hydroxide solution is added to the residue until reaching a pH value of 8. The mixture is allowed to stand in refrigerator for a night. The crystals are filtered, washed with water and dried. In this way 1.0 g (63%) of the aimed compound is obtained.

Workup

  1. additionis added in 30 minutes
  2. temperaturereflux
  3. customevaporated in vacuo to third of its volume
  4. additiona 40% aqueous sodium hydroxide solution is added to the residue
  5. waitto stand in refrigerator for a night
  6. filtrationThe crystals are filtered
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-81cf548a2dde46caa3c84c40e1ce9f9a
Source dataset
uspto-grants-1988_10
Patent number
US04780537

Reaction notes

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