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

HRID 1958444Notes

Reaction equation

HRID 1958444 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-4878eaaddbc94ae2a8637913bd73c507
Source dataset
uspto-grants-2013_04
Patent number
US08410119B2

Reaction notes

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