Water → 2,7-Dichloro-5-trifluoromethyl-thiazolo[4,5-d]pyrimidine

HRID 908615Notes

Reaction equation

HRID 908615 reaction equation
[Cl:1][C:2]1[S:3][C:4]2[C:9](O)=[N:8][C:7]([C:11]([F:14])([F:13])[F:12])=[N:6][C:5]=2[N:15]=1.O.P(Cl)(Cl)([Cl:19])=O>>[Cl:1][C:2]1[S:3][C:4]2[C:9]([Cl:19])=[N:8][C:7]([C:11]([F:14])([F:13])[F:12])=[N:6][C:5]=2[N:15]=1

Participants

4

Reactant 3

HCID 962WaterHCID 24813Phosphorus oxychlorideHCID 178517789HCID 178517789, compound

Product 1

HCID 597038262,7-Dichloro-5-trifluoromethyl-thiazolo[4,5-d]pyrimidine

Procedure

To a solution of the compound (1.35 g) obtained in Step 7 in phosphorus oxychloride (20 ml) was added water (190 mg) with stirring under ice-cooling, and the mixture was stirred at 100° C. for 3 hr. The reaction mixture was concentrated under reduced pressure, and partitioned by adding chloroform and water. The organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, filtrated, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:10) to give the title compound (1.17 g).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at 100° C. for 3 hr
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. custompartitioned
  5. additionby adding chloroform and water
  6. washThe organic layer was washed successively with water and saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltrated
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:10)

Sources & evidence

ORD record
ord-2e4c8bce905746708ca12f4f7119b058
Source dataset
uspto-grants-2011_09
Patent number
US08017612B2

Reaction notes

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