Phosphorus oxychloride → 4-Chloro-5-phenyl-6-(4-(2-(pyrrolidin-1-yl)ethoxy)phenyl)furo[2,3-d]pyrimidine

HRID 502645Notes

Reaction equation

HRID 502645 reaction equation
[C:1]1([C:7]2[C:15]3[C:14](=O)[NH:13][CH:12]=[N:11][C:10]=3[O:9][C:8]=2[C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][N:26]3[CH2:30][CH2:29][CH2:28][CH2:27]3)=[CH:19][CH:18]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Cl)(Cl)([Cl:33])=O>C1C=CC=CC=1>[Cl:33][C:14]1[C:15]2[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[C:8]([C:17]3[CH:18]=[CH:19][C:20]([O:23][CH2:24][CH2:25][N:26]4[CH2:27][CH2:28][CH2:29][CH2:30]4)=[CH:21][CH:22]=3)[O:9][C:10]=2[N:11]=[CH:12][N:13]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 586032805-phenyl-6-(4-(2-(pyrrolidin-1-yl)ethoxy)phenyl)furo[2,3-d]pyrimidin-4 (3H)-one

Product 1

HCID 586032684-Chloro-5-phenyl-6-(4-(2-(pyrrolidin-1-yl)ethoxy)phenyl)furo[2,3-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Into a 50 mL round bottom flask was placed 5-phenyl-6-(4-(2-(pyrrolidin-1-yl)ethoxy)phenyl)furo[2,3-d]pyrimidin-4 (3H)-one 46 (132 mg, 0.329 mmol), and benzene (40 mL). The flask was equipped with a magnetic stir bar, dean-stark trap and a reflux condenser. The reaction was brought to reflux with some of the solvent having been distilled into the dean-stark trap. The reaction was allowed to cool to room temperature and phosphorous oxychloride (300 mg, 1.96 mmol) was added dropwise. The reaction was heated at reflux for 20 hours.

Workup

  1. customInto a 50 mL round bottom flask was placed
  2. customThe flask was equipped with a magnetic stir bar, dean-stark trap and a reflux condenser
  3. temperatureto reflux with some of the solvent
  4. distillationhaving been distilled into the dean-stark trap
  5. temperatureThe reaction was heated
  6. temperatureat reflux for 20 hours

Sources & evidence

ORD record
ord-ecd68025f2d54284903088210e28f3a1
Source dataset
uspto-grants-2010_08
Patent number
US07776867B2

Reaction notes

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