Phosphorus oxychloride → 4-Chloro-6-iodo-5-phenyl-furo[2,3-d]pyrimidine

HRID 502635Notes

Reaction equation

HRID 502635 reaction equation
[I:1][C:2]1[O:11][C:5]2[N:6]=[CH:7][NH:8][C:9](=O)[C:4]=2[C:3]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.P(Cl)(Cl)([Cl:20])=O>>[Cl:20][C:9]1[C:4]2[C:3]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:2]([I:1])[O:11][C:5]=2[N:6]=[CH:7][N:8]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 586032796-iodo-5-phenyl-3H-furo[2,3-d]pyrimidin-4-one

Product 1

HCID 586032664-Chloro-6-iodo-5-phenyl-furo[2,3-d]pyrimidine

Procedure

Compound 11 (0.8 g, 2.35 mmol) was refluxed in phosphorous oxychloride (12 mL) for 90 minutes. The reaction mixture was concentrated and diluted with ice-cold water, extracted with dichloromethane. The organic layer was washed with water and dried over MgSO4. The organic solvent upon concentration provided a pale solid, which on trituration with MeOH provided the title compound 12.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with ice-cold water
  3. extractionextracted with dichloromethane
  4. washThe organic layer was washed with water
  5. dry with materialdried over MgSO4
  6. concentrationThe organic solvent upon concentration
  7. customprovided a pale solid, which on trituration with MeOH

Sources & evidence

ORD record
ord-deff769252dd477f80deecf67d5ef062
Source dataset
uspto-grants-2010_08
Patent number
US07776867B2

Reaction notes

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