Triethylamine → 4-Chloro-2-(methylthio)pyrazolo[1,5-a][1,3,5]triazine

HRID 624765Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 624765
[CH3:1][S:2][C:3]1[NH:8][C:7](=O)[N:6]2[N:10]=[CH:11][CH:12]=[C:5]2[N:4]=1.P(Cl)(Cl)([Cl:15])=O.C(N(CC)CC)C>C(#N)C>[Cl:15][C:7]1[N:6]2[N:10]=[CH:11][CH:12]=[C:5]2[N:4]=[C:3]([S:2][CH3:1])[N:8]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 1354442592-(Methylthio)pyrazolo[1,5-a][1,3,5]triazin-4(3H)-one

Produkt 1

HCID 129161154-Chloro-2-(methylthio)pyrazolo[1,5-a][1,3,5]triazineAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

In a round bottom flask equipped with a magnetic stirbar, 2-(methylthio)pyrazolo[1,5-a][1,3,5]triazin-4(3H)-one (1.0 eq, 10.43 g, 57.24 mmol) was suspended in acetonitrile (100 ml). Phosphorus oxychloride (4.0 eq, 21 ml, 229.4 mmol) and triethylamine (1.05 eq, 8.4 ml, 60.27 mmol) were added and the mixture stirred at reflux for 3.5 hours, at which time LCMS indicated completion of the reaction. The mixture was cooled down and slowly poured into crushed ice (final total volume of about 600 ml). The solid was filtered, washed with water and dried in a vacuum oven to afford 4-chloro-2-(methylthio)pyrazolo[1,5-a][1,3,5]triazine as a tan solid (8.15 g, 71% yield). LCMS (ES): >97% pure, m/z 201 [M+H]+.

Aufarbeitung

  1. temperatureat reflux for 3.5 hours, at which time LCMS
  2. customcompletion of the reaction
  3. temperatureThe mixture was cooled down
  4. additionslowly poured
  5. custominto crushed ice (final total volume of about 600 ml)
  6. filtrationThe solid was filtered
  7. washwashed with water
  8. customdried in a vacuum oven

Quellen und Nachweise

ORD-Eintrag
ord-cd77b86bfe6c48ef917c8241596b5ffa
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09303033B2

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