Benzene → 4-Chloro-5-phenylfuro[2,3-d]pyrimidine

HRID 502636Notes

Reaction equation

HRID 502636 reaction equation
C1(C2C(=O)[C:11]34[CH2:18][CH2:17][O:16][C:12]3=[N:13][CH:14]=[N:15][C:10]4=CC=2)C=CC=CC=1.P(Cl)(Cl)([Cl:23])=O.[CH:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>>[Cl:23][C:10]1[C:11]2[C:18]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:17][O:16][C:12]=2[N:13]=[CH:14][N:15]=1

Participants

4

Reactant 3

HCID 241BenzeneHCID 24813Phosphorus oxychlorideHCID 684608515-Phenylfuro[2,3-d]benzopyrimidin-4 (3h)-one

Product 1

HCID 594278334-Chloro-5-phenylfuro[2,3-d]pyrimidine

Procedure

Into a 100 mL round bottom flask was placed 5-phenylfuro[2,3-d]benzopyrimidin-4 (3H)-one (1.12 g, 5.3 mmol) and benzene (75 mL). The flask was equipped with a stir bar, reflux condenser, and Dean-Stark trap, and the reaction was allowed to reflux with stirring for 1 hour azeotropically removing the water formed. The reaction was cooled to room temperature. Phosphorus oxychloride was added (2.43 g, 15.9 mmol) dropwise, the flask equipped with a reflux condenser and the reaction was heated at reflux for 20 hours with stirring.

Workup

  1. customInto a 100 mL round bottom flask was placed
  2. customThe flask was equipped with a stir bar
  3. temperaturereflux condenser
  4. temperatureto reflux
  5. customazeotropically removing the water
  6. customformed
  7. customthe flask equipped with a reflux condenser
  8. temperaturethe reaction was heated
  9. temperatureat reflux for 20 hours
  10. stirringwith stirring

Sources & evidence

ORD record
ord-a2e284d50420409eb7d56b4af768861d
Source dataset
uspto-grants-2010_08
Patent number
US07776867B2

Reaction notes

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