Phosphorus oxychloride → 4-Chloro-7-mesityl-2,5-dimethyl-7H-pyrrolo[2,3-d]pyrimidine

HRID 1884340Notes

Reaction equation

HRID 1884340 reaction equation
[CH3:1][C:2]1[NH:3][C:4](=O)[C:5]2[C:10]([CH3:11])=[CH:9][N:8]([C:12]3[C:17]([CH3:18])=[CH:16][C:15]([CH3:19])=[CH:14][C:13]=3[CH3:20])[C:6]=2[N:7]=1.O=P(Cl)(Cl)[Cl:24]>>[Cl:24][C:4]1[C:5]2[C:10]([CH3:11])=[CH:9][N:8]([C:12]3[C:17]([CH3:18])=[CH:16][C:15]([CH3:19])=[CH:14][C:13]=3[CH3:20])[C:6]=2[N:7]=[C:2]([CH3:1])[N:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 135461719HCID 135461719, compound

Product 1

HCID 107805364-Chloro-7-mesityl-2,5-dimethyl-7H-pyrrolo[2,3-d]pyrimidine

Procedure

A mixture of the compound of step C (1.030 g, 3.67 mmol) and POCl3 (3 ml) was heated at reflux for 2.5 hours and cooled. The reaction mixture was poured into ice-water and extracted with ethyl acetate. The organic layer was washed with dilute sodium bicarbonate and brine, dried over anhydrous sodium sulfate, and concentrated to dryness to give the title compound as a tan solid which was purified through silica gel to give an off-white solid. 1H NMR (CDCl3) δ 1.90(s, 6H), 2.35(s, 3H), 2.50(s, 3H), 2.65(s, 3H), 6.78(s, 1H), 7.00(s, 2H) ppm.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2.5 hours
  3. temperaturecooled
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with dilute sodium bicarbonate and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-bcef52d38add4d6f8982476fd10cd9e2
Source dataset
uspto-grants-2004_07
Patent number
US06765008B1

Reaction notes

Loading…