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

HRID 502640Notes

Reaction equation

HRID 502640 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>>[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

3

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

Procedure

Compound 26 (60 mg, 0.149 mmol) was refluxed in phosphorous oxychloride (2 mL) for 1 h. The reaction mixture was concentrated and diluted with ice-cold water, brought to pH ˜8 with slow addition of saturated NaHCO3 and extracted with dichloromethane. The organic layer was dried over Na2SO4 and concentrated to afford 27, which was used in Step 3 without purification.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with ice-cold water
  3. additionbrought to pH ˜8 with slow addition of saturated NaHCO3
  4. extractionextracted with dichloromethane
  5. dry with materialThe organic layer was dried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b634d14afa284b03955375b35a5415c0
Source dataset
uspto-grants-2010_08
Patent number
US07776867B2

Reaction notes

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