Hydrochloric Acid → HCID 58196600, Verbindung
Reaktionsgleichung
[CH:1]1([NH:4][C:5]2[N:10]3[N:11]=[CH:12][CH:13]=[C:9]3[N:8]=[C:7]([S:14][CH3:15])[N:6]=2)[CH2:3][CH2:2]1.P(Cl)(Cl)(Cl)=O.[OH-].[Na+].Cl.CN([CH:27]=[O:28])C>>[CH:1]1([NH:4][C:5]2[N:10]3[N:11]=[CH:12][C:13]([CH:27]=[O:28])=[C:9]3[N:8]=[C:7]([S:14][CH3:15])[N:6]=2)[CH2:3][CH2:2]1Komponenten
Reaktionsbedingungen
- Temperatur
- 70 °C
Versuchsvorschrift
N-Cyclopropyl-2-(methylthio)pyrazolo[1,5-a][1,3,5]triazin-4-amine (1.0 eq, 3.10 g, 14.00 mmol) was dissolved in anhydrous DMF (50 ml) under nitrogen atmosphere. Phosphorus oxychloride (5.0 eq, 6.4 ml, 69.9 mmol) was added dropwise over 5 minutes. Internal temperature rose to 45° C. The reaction was stirred in an oil bath at 70° C. for 4.5 hours. The mixture was cooled down and added dropwise into a solution of 6N NaOH (150 ml) chilled with an ice bath. The rate of addition was adjusted to maintain the internal temperature of the aqueous NaOH below 16° C. At the end of the addition, the mixture was neutralized by slow addition of 6N HCl to reach pH=5-6. The resulting solid was filtered, washed with water and dried in a vacuum oven overnight. 4-(cyclopropylamino)-2-(methylthio)pyrazolo[1,5-a][1,3,5]triazine-8-carbaldehyde was isolated as tan solid (9.26 g, 93%). LCMS (ES):>95% pure, m/z 250 [M+H]+.
Aufarbeitung
- customrose to 45° C
- temperatureThe mixture was cooled down
- temperaturechilled with an ice bath
- additionThe rate of addition
- additionAt the end of the addition
- filtrationThe resulting solid was filtered
- washwashed with water
- customdried in a vacuum oven overnight
Quellen und Nachweise
- ORD-Eintrag
- ord-0194f12a1cbb4abca3aeb09b5f7731a7
- Quelldatensatz
- uspto-grants-2013_11
- Patentnummer
- US08575177B2
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