Phosphorus oxychloride → Ethyl 2-(3-benzenesulphonyl-7-chloro-5-methyl-2-methylsulphanyl-pyrazolo[1,5-a]pyrimidin-6-yl)-aceate

HRID 636428Notes

Reaction equation

HRID 636428 reaction equation
[C:1]1([S:7]([C:10]2[C:11]([S:27][CH3:28])=[N:12][N:13]3[C:18](O)=[C:17]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:16]([CH3:26])=[N:15][C:14]=23)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O=P(Cl)(Cl)[Cl:31]>>[C:1]1([S:7]([C:10]2[C:11]([S:27][CH3:28])=[N:12][N:13]3[C:18]([Cl:31])=[C:17]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:16]([CH3:26])=[N:15][C:14]=23)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178470704HCID 178470704, compound

Product 1

HCID 21255058Ethyl 2-(3-benzenesulphonyl-7-chloro-5-methyl-2-methylsulphanyl-pyrazolo[1,5-a]pyrimidin-6-yl)-aceateYield 94%

Procedure

A suspension of 1.5 g (3.56 mmol) of ethyl 2-(3-benzenesulphonyl-7-hydroxy-5-methyl -2-methylsulphanyl-pyrazolo[1,5-a]pyrimidin-6-yl)-acetate in 30 ml of POCl3 was heated at reflux for 4 hrs. 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 70 ml of CH2Cl2, and the organic phases were dried (MgSO4), filtered and evaporated.Chroma-tography (SiO2, CH2Cl220:1) of the residue yielded 1.0 g (94%) of ethyl 2-(3-benzenesulphonyl-7-chloro-5-methyl-2-methylsulphanyl-pyrazolo[1,5-a]pyrimidin-6-yl)-aceate as a pale yellow solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 hrs
  3. customevaporated
  4. additionThe residue was treated with 100 ml of ice-water
  5. extractionThe aqueous phase was extracted three times with 70 ml of CH2Cl2
  6. dry with materialthe organic phases were dried (MgSO4)
  7. filtrationfiltered

Sources & evidence

ORD record
ord-7e96ad49fad947d3a0ec1274dbf2594c
Source dataset
uspto-grants-2001_02
Patent number
US06194410B1

Reaction notes

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