Phosphorus oxychloride → 4-chloro-N-ethyl-6-propylpyrimidin-2-amine

HRID 1588487Notes

Reaction equation

HRID 1588487 reaction equation
[CH2:1]([NH:3][C:4]1[N:9]=[C:8](O)[CH:7]=[C:6]([CH2:11][CH2:12][CH3:13])[N:5]=1)[CH3:2].P(Cl)(Cl)([Cl:16])=O>>[Cl:16][C:8]1[CH:7]=[C:6]([CH2:11][CH2:12][CH3:13])[N:5]=[C:4]([NH:3][CH2:1][CH3:2])[N:9]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178439469HCID 178439469, compound

Product 1

HCID 197542474-chloro-N-ethyl-6-propylpyrimidin-2-amineYield 90%

Conditions

Temperature
100 °C

Procedure

A mixture of 2-ethylamino-4-hydroxy-6-propylpyrimidine (1.81 g, 10 mM) and phosphorus oxychloride (15 ml) was heated at 100° C. for 18 hours. The excess of phosphorus oxychloride was removed under reduced pressure and the residual was decomposed with ice-water (50 ml). The solution was made basic with concentrated aqueous ammonia and extracted with ethyl acetate (3×50 ml). The extracts were combined, dried and the solvent evaporated to give 4-chloro-2-ethylamino-6-propylpyrimidine (1.79 g; 90% yield) as an oil which was used without purification.

Workup

  1. customThe excess of phosphorus oxychloride was removed under reduced pressure
  2. extractionextracted with ethyl acetate (3×50 ml)
  3. customdried
  4. customthe solvent evaporated

Sources & evidence

ORD record
ord-9d04d55e8596496c82eef8fb0afb6211
Source dataset
uspto-grants-1993_06
Patent number
US05223505

Reaction notes

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