Phosphorus oxychloride → 3-Benzenesulphonyl-7-chloro-5-methoxymethyl-2-methylsulphanyl-pyrazolo[1,5-a]pyrimidine

HRID 636435

Reaktionsgleichung

Reaktionsgleichung von HRID 636435
[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]=1

Komponenten

4

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 178494547HCID 178494547, Verbindung

Produkt 1

HCID 212549933-Benzenesulphonyl-7-chloro-5-methoxymethyl-2-methylsulphanyl-pyrazolo[1,5-a]pyrimidineAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7061N,N-DiethylanilineLösungsmittel

Versuchsvorschrift

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°.

Aufarbeitung

  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 100 ml of CH2Cl2,and the organic phases
  6. dry with materialwere dried (MgSO4)
  7. filtrationfiltered
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-64ed753f56ed48a1a3bd9bd5c4f7ba90
Quelldatensatz
uspto-grants-2001_02
Patentnummer
US06194410B1

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