Phosphorus oxychloride → 7-chloro-2-phenyl[1,3]oxazolo[5,4-d]pyrimidine

HRID 1468990Notes

Reaction equation

HRID 1468990 reaction equation
[C:1]1([C:7]2[O:8][C:9]3[N:10]=[CH:11][N:12]=[C:13](O)[C:14]=3[N:15]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O=P(Cl)(Cl)[Cl:19]>>[Cl:19][C:13]1[C:14]2[N:15]=[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[O:8][C:9]=2[N:10]=[CH:11][N:12]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178518063HCID 178518063, compound

Product 1

HCID 2831667-chloro-2-phenyl[1,3]oxazolo[5,4-d]pyrimidineYield 67%

Procedure

2-Phenyl-oxazolo[5,4-d]pyrimidin-7-ol (0.10 g, 0.43 mmol) was dissolved in 3 mL POCl3, and the mixture was refluxed under nitrogen for 6 hours. The reaction mixture was cooled to room temperature and poured onto ice water. The resulting mixture was extracted by CH2Cl2. The combined organic layers were concentrated and the residue was purified by column chromatography (EtOAc:hexanes=1:10) to afford the title compound as a white solid (73 mg, 67%). 1H NMR 400 MHz (CDCl3) δ 8.82 (s, 1H), 7.35-7.32 (m, 2H), 7.68-7.57 (m, 3H). LC-MS (ESI) m/z 232.0 (M+1).

Workup

  1. temperaturethe mixture was refluxed under nitrogen for 6 hours
  2. additionpoured onto ice water
  3. extractionThe resulting mixture was extracted by CH2Cl2
  4. concentrationThe combined organic layers were concentrated
  5. customthe residue was purified by column chromatography (EtOAc:hexanes=1:10)

Sources & evidence

ORD record
ord-c19c7849b50f4a3bb7710be794f01772
Source dataset
uspto-grants-2015_04
Patent number
US09006252B2

Reaction notes

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