Phosphorus oxychloride → HCID 22313247, compound

HRID 989718Notes

Reaction equation

HRID 989718 reaction equation
[NH2:1][C:2]1[N:7]=[C:6](O)[C:5]([CH2:9][CH2:10][O:11][CH3:12])=[C:4]([CH3:13])[N:3]=1.P(Cl)(Cl)([Cl:16])=O>>[Cl:16][C:6]1[C:5]([CH2:9][CH2:10][O:11][CH3:12])=[C:4]([CH3:13])[N:3]=[C:2]([NH2:1])[N:7]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178494790HCID 178494790, compound

Product 1

HCID 22313247HCID 22313247, compoundYield 30.3%

Procedure

A mixture of 2-amino-5-(2-methoxyethyl)-6-methylpyrimidine-4-ol (600 mg, 3.27 mmol) and phosphorus oxychloride (6 ml) was kept at 90° C. for 5.5 hours. The reaction mixture was concentrated in vacuo. Was added to the residue and an aqueous ammonia solution was cautiously added. The mixture was extracted with chloroform and the organic layer was washed with saturated brine, dried over sodium sulfate and the solvent was concentrated. The residue was purified by silica gel column chromatography (chloroform: ethyl acetate=8:2) to give the object compound (200 mg, 30.3%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionWas added to the residue
  3. additionan aqueous ammonia solution was cautiously added
  4. extractionThe mixture was extracted with chloroform
  5. washthe organic layer was washed with saturated brine
  6. dry with materialdried over sodium sulfate
  7. concentrationthe solvent was concentrated
  8. customThe residue was purified by silica gel column chromatography (chloroform: ethyl acetate=8:2)

Sources & evidence

ORD record
ord-b4b60c7e9c2a4783affd5888f48e1196
Source dataset
uspto-grants-2002_10
Patent number
US06458798B1

Reaction notes

Loading…