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

HRID 1416915Notes

Reaction equation

HRID 1416915 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 δ 8.45 (br s, 2 H, NH2, exchange with D2O), 9.03 (s, 1H, 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-d70d6a303eb340b08885f312309074d3
Source dataset
uspto-grants-1999_06
Patent number
US05916894

Reaction notes

Loading…