Reaction equation
[C:1]1([S:7]([C:10]2[C:11]([S:23][CH3:24])=[N:12][N:13]3[C:18](O)=[CH:17][C:16]([CH2:20][O:21][CH3:22])=[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:27]>CCN(C1C=CC=CC=1)CC>[C:1]1([S:7]([C:10]2[C:11]([S:23][CH3:24])=[N:12][N:13]3[C:18]([Cl:27])=[CH:17][C:16]([CH2:20][O:21][CH3:22])=[N:15][C:14]=23)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1Participants
4
Procedure
A suspension of 2.5 g (6.8 mmol) of 3-benzenesulphonyl-5-methoxymethyl-2-methylsulphanyl-pyrazolo[1,5-a]pyrimidin-7-ol in 40 ml of POCl3 and 20 ml of diethylaniline 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 100 ml of CH2Cl2,and the organic phases were dried (MgSO4), filtered and evaporated. Chromatography (SiO2, CH2Cl2/MeOH 20:1) yielded 2.1 g (79%) of 3-benzenesulphonyl-7-chloro-5-methoxymethyl-2-methylsulphanyl-pyrazolo[1,5-a]pyrimidine as a pale yellow powder, m.p. 194-197°.
Workup
- temperaturewas heated
- temperatureat reflux for 1 hr
- customevaporated
- additionThe residue was treated with 100 ml of ice-water
- extractionThe aqueous phase was extracted three times with 100 ml of CH2Cl2,and the organic phases
- dry with materialwere dried (MgSO4)
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-64ed753f56ed48a1a3bd9bd5c4f7ba90
- Source dataset
- uspto-grants-2001_02
- Patent number
- US06194410B1
Linked notes
Loading…