Phosphorus oxychloride → 7-Chloro-3-[4-(methanesulfonyl)phenyl][1,2]oxazolo[4,5-d]pyrimidine

HRID 719527Notes

Reaction equation

HRID 719527 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:15]3[N:16]=[CH:17][N:18]=[C:19](O)[C:14]=3[O:13][N:12]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].O=P(Cl)(Cl)[Cl:23]>>[Cl:23][C:19]1[C:14]2[O:13][N:12]=[C:11]([C:8]3[CH:9]=[CH:10][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:6][CH:7]=3)[C:15]=2[N:16]=[CH:17][N:18]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178504702HCID 178504702, compound

Product 1

HCID 218975727-Chloro-3-[4-(methanesulfonyl)phenyl][1,2]oxazolo[4,5-d]pyrimidineYield 80.1%

Procedure

3-(4-Methanesulfonyl-phenyl)-isoxazolo[4,5-d]pyrimidin-7-ol (0.5 g, 1.7 mmol) was suspended in POCl3 (10 mL) and refluxed for 12 h. The reaction was poured into ice carefully and precipitates filtered. The solid was dissolved in ethyl acetate (15 mL) and purified under SiO2 with 30% ethyl acetate in hexane to afford the desired compound (0.42 g, 80.1%).

Workup

  1. temperaturerefluxed for 12 h
  2. additionThe reaction was poured into ice carefully
  3. customprecipitates
  4. filtrationfiltered
  5. dissolutionThe solid was dissolved in ethyl acetate (15 mL)
  6. custompurified under SiO2 with 30% ethyl acetate in hexane

Sources & evidence

ORD record
ord-6f17567c0fcd4a67b586da8b91488160
Source dataset
uspto-grants-2006_11
Patent number
US07132426B2

Reaction notes

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