Reaktion #711996

Reaktionsgleichung

4-(1H-pyrazol-1-yl)aniline

Cs2CO3

tert-butyl 5-chloro-3-formyl-2-methylpyrazolo[1,5-a]pyrimidin-7-yl(cyclopropyl)carbamate

BINAP

→

5-(4-(1H-pyrazol-1-yl)phenylamino)-7-(cyclopropylamino)-2-methylpyrazolo[1,5-a]pyrimidine-3-carbaldehyde

Ausbeute 23.0%

Lösungsmittel

Et2O

1,4-dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe mixture was sealed
2. 2
   Sonstigeirradiated at 110° C. for 60 min in the microwave
3. 3
   Filtrationthe solution was filtered
4. 4
   EinengenThe filtrate was concentrated in vacuo
5. 5
   workup.DISSOLUTIONThe crude residue was dissolved in dichloromethane (1.5 mL)
6. 6
   Einengenthe solution was concentrated under a stream of air
7. 7
   SonstigeThe crude material was purified by silica gel chromatography (15% acetone/dichloromethane)

Vorschrift

To 4-(1H-pyrazol-1-yl)aniline (54 mg, 0.34 mmol), Cs2CO3 (130 mg, 0.4 mmol) were added to tert-butyl 5-chloro-3-formyl-2-methylpyrazolo[1,5-a]pyrimidin-7-yl(cyclopropyl)carbamate (100 mg, 0.29 mmol) dissolved in 1,4-dioxane (1.1 mL). Racemic BINAP (11 mg, 0.017 mmol) and palladium(II) acetate (8 mg, 0.011 mmol) were then added. The mixture was sealed and irradiated at 110° C. for 60 min in the microwave. Et2O (3 mL) was added and the solution was filtered. The filtrate was concentrated in vacuo. The crude residue was dissolved in dichloromethane (1.5 mL) and trifluoroacetic acid (1.5 mL). After stirring at room temperature for 1 hour, the solution was concentrated under a stream of air. The crude material was purified by silica gel chromatography (15% acetone/dichloromethane) to yield the product, 5-(4-(1H-pyrazol-1-yl)phenylamino)-7-(cyclopropylamino)-2-methylpyrazolo[1,5-a]pyrimidine-3-carbaldehyde (24 mg, 23% yield). LCMS (M+1=374)

Quelle