Phosphorus oxychloride → 3-Benzenesulphonyl-7-chloro-5-(4-methyl-piperazin-1-ylmethyl)-2-methylsulphanyl-pyrazolo[1,5-a]pyrimidine

HRID 636452Notes

Reaction equation

HRID 636452 reaction equation
[C:1]1([S:7]([C:10]2[C:11]([S:28][CH3:29])=[N:12][N:13]3[C:18](O)=[CH:17][C:16]([CH2:20][N:21]4[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]4)=[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:32]>>[C:1]1([S:7]([C:10]2[C:11]([S:28][CH3:29])=[N:12][N:13]3[C:18]([Cl:32])=[CH:17][C:16]([CH2:20][N:21]4[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]4)=[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 178503604HCID 178503604, compound

Product 1

HCID 212550513-Benzenesulphonyl-7-chloro-5-(4-methyl-piperazin-1-ylmethyl)-2-methylsulphanyl-pyrazolo[1,5-a]pyrimidineYield 98%

Procedure

A suspension of 4.0 g (9 mmol) of 3-benzenesulphonyl-5-(4-methyl-piperazin-1-ylmethyl)-2-methylsulphanyl-pyrazolo[1,5-a]pyrimidin-7-ol in 100 ml of POCl3 was heated at reflux for 3 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 150 ml of CH2Cl2 and the organic phases were dried (MgSO4), filtered and evaporated. Chroma-tography (SiO2CH2Cl2/MeOH 10:1) of the residue yielded 4.0 g (98%) of 3-benzenesulphonyl-7-chloro-5-(4-methyl-piperazin-1-ylmethyl)-2-methylsulphanyl-pyrazolo[1,5-a]pyrimidine as a pale brown powder, m.p. 113-116°.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hrs
  3. customevaporated
  4. additionThe residue was treated with 100 ml of ice-water
  5. extractionThe aqueous phase was extracted three times with 150 ml of CH2Cl2
  6. dry with materialthe organic phases were dried (MgSO4)
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-5777293b18964bf8bf6d27f9c2d1e97d
Source dataset
uspto-grants-2001_02
Patent number
US06194410B1

Reaction notes

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