Phosphorus oxychloride → 7-Chloro-5-methyl-2-methylsulphanyl-3-(toluene-4-sulphonyl)-pyrazolo[1,5-a]pyrimidine

HRID 636392Notes

Reaction equation

HRID 636392 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6](O)[N:5]2[N:9]=[C:10]([S:22][CH3:23])[C:11]([S:12]([C:15]3[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=3)(=[O:14])=[O:13])=[C:4]2[N:3]=1.O=P(Cl)(Cl)[Cl:26]>>[Cl:26][C:6]1[N:5]2[N:9]=[C:10]([S:22][CH3:23])[C:11]([S:12]([C:15]3[CH:16]=[CH:17][C:18]([CH3:21])=[CH:19][CH:20]=3)(=[O:14])=[O:13])=[C:4]2[N:3]=[C:2]([CH3:1])[CH:7]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178503607HCID 178503607, compound

Product 1

HCID 212550447-Chloro-5-methyl-2-methylsulphanyl-3-(toluene-4-sulphonyl)-pyrazolo[1,5-a]pyrimidineYield 95%

Procedure

A suspension of 3.8 g (10.8 mmol) of 5-methyl-2-methylsulphanyl-3-(toluene-4-sulphonyl)-pyrazolo[1,5-a]pyrimidin-7-ol in 20 l of POCl3 was heated at reflux for 1 hr. The reaction solution was cooled to RT and evaporated. The residue was treated with 100 ml of ice-water and the pH value of the solution was adjusted to 8 with sat. NaHCO3 solution. The aqueous phase was extracted three times with CH2Cl2, and the organic phases were dried (MgSO4), filtered and evaporated. Chromatography (SiO2, CH2Cl2/AcOEt 25:1) of the residue yielded 3.8 g (95%) of 7-chloro-5-methyl-2-methylsulphanyl-3-(toluene-4-sulphonyl)-pyrazolo[1,5-a]pyrimidine as pale yellow crystals, m.p. 197-198°.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 hr
  3. customevaporated
  4. additionThe residue was treated with 100 ml of ice-water
  5. extractionThe aqueous phase was extracted three times with CH2Cl2
  6. dry with materialthe organic phases were dried (MgSO4)
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-31df9f08c2e5456f8662d7167d12c52d
Source dataset
uspto-grants-2001_02
Patent number
US06194410B1

Reaction notes

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