Phosphorus oxychloride → 4-chloro-5-nitropyrimidin-2-amine

HRID 619220Notes

Reaction equation

HRID 619220 reaction equation
[NH2:1][C:2]1[N:7]=[C:6](O)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.P(Cl)(Cl)([Cl:14])=O>>[NH2:1][C:2]1[N:7]=[C:6]([Cl:14])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178508524HCID 178508524, compound

Product 1

HCID 3199954-chloro-5-nitropyrimidin-2-amine

Procedure

A suspension of 2-amino-4-hydroxy-5-nitropyrimidine (5.0 g, 32.1 mmol) in phosphorous oxychloride (100 mL) was refluxed overnight, and the excess phosphorous oxychloride was evaporated under reduced pressure. The residue was mixed with ice (100 g) in an ice-bath, and the mixture was neutralized with concentrated aqueous sodium carbonate solution. A yellow precipitate was collected by filtration and washed with water: yield, 1.39 g (25%); mp 191-194° C. dec.; 1H NMR d 8.45 (br s, 2 H, NH2, exchange with D2O), 9.03 (s, 1 H, H-6); MS (EI) calcd. m/z for C4H3N4O235Cl 173.9944, found 173.9934; calcd. m/z for C4H3N4O237Cl 175.9915, found 175.9916.

Workup

  1. temperaturewas refluxed overnight
  2. customthe excess phosphorous oxychloride was evaporated under reduced pressure
  3. additionThe residue was mixed with ice (100 g) in an ice-bath
  4. filtrationA yellow precipitate was collected by filtration
  5. washwashed with water
  6. customyield

Sources & evidence

ORD record
ord-db49e4cd90cf4217ac77488d778a468b
Source dataset
uspto-grants-1999_09
Patent number
US05958932

Reaction notes

Loading…