Nitric Acid → 2-Amino-6-chloro-5-nitro-3,4-dihydropyrimidin-4-one

HRID 1355843Notes

Reaction equation

HRID 1355843 reaction equation
O.[NH2:2][C:3]1[N:8]=[C:7]([OH:9])[CH:6]=[C:5]([Cl:10])[N:4]=1.[N+:11]([O-])([OH:13])=[O:12]>S(=O)(=O)(O)O>[NH2:2][C:3]1[NH:8][C:7](=[O:9])[C:6]([N+:11]([O-:13])=[O:12])=[C:5]([Cl:10])[N:4]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 178508975HCID 178508975, compound

Product 1

HCID 1354086932-Amino-6-chloro-5-nitro-3,4-dihydropyrimidin-4-oneYield 99%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Following the method of O'Brien and Cheng (J. Med. Chem. 1966, 9, 573), to a stirred solution of 10.0 g (61.1 mmol) 2-amino-6-chloro-4-pyrimidinol monohydrate in 46 ml 98% sulfuric acid was added dropwise 9 ml 65% nitric acid at a rate such that the reaction temperature remainded around 40° C. After the addition was complete, stirring was continued for 1 hour at room temperature. The reaction mixture was then poured onto 150 ml ice-water and the resulting crystals were collected by filtration and washed sequentially with water, ethanol and ether to afford 12.6 g (99%) 2-amino-6-chloro-5-nitro-3H-pyrimidin-4-one as a light yellow crystalline solid. ES-MS m/e (%): 191 (M+H+, 100).

Workup

  1. customremainded around 40° C
  2. additionAfter the addition
  3. filtrationthe resulting crystals were collected by filtration
  4. washwashed sequentially with water, ethanol and ether

Sources & evidence

ORD record
ord-98d0306e0b9a4613a431838cf082cbbb
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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