Reaktion #418255

Reaktionsgleichung

Na2CO3

[3-(2-Chloro-5-fluoro-pyrimidin-4-ylamino)-6,6-dimethyl-4,6-dihydro-1H-pyrrolo[3,4-c]pyrazol-5-yl]-(4-fluoro-1-methyl-piperidin-4-yl)-methanone

DME

4,4,5,5-tetramethyl-2-vinyl-1,3,2 dioxaborolane

→

desired product

5-[(4-fluoro-1-methylpiperidin-4-yl)carbonyl]-N-(5-fluoro-2-vinylpyrimidin-4-yl)-6,6-dimethyl-1,4,5,6-tetrahydropyrrolo[3,4-c]pyrazol-3-amine

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONTo a pressure vessel was added
2. 2
   SonstigeThe reaction mixture was purged with argon for 2 min
3. 3
   EinengenThe volatiles were concentrated in vacuo
4. 4
   workup.DISSOLUTIONthe residue redissolved in EtOAc (15 mL)
5. 5
   WaschenThe organic layer was washed with water (10 mL)
6. 6
   Trocknendried over MgSO4
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated

Vorschrift

To a pressure vessel was added starting material [3-(2-Chloro-5-fluoro-pyrimidin-4-ylamino)-6,6-dimethyl-4,6-dihydro-1H-pyrrolo[3,4-c]pyrazol-5-yl]-(4-fluoro-1-methyl-piperidin-4-yl)-methanone (0.375 g, 0.881 mmol), 4,4,5,5-tetramethyl-2-vinyl-1,3,2 dioxaborolane (0.407 g, 2.64 mmol), Na2CO3 (0.280 g, 2.64 mmol) and dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (0.144 g, 0.176 mmol) followed by DME (10 mL) and water (2 mL). The reaction mixture was purged with argon for 2 min, then heat to 100° C. for 15 h. The volatiles were concentrated in vacuo and the residue redissolved in EtOAc (15 mL). The organic layer was washed with water (10 mL), dried over MgSO4, filtered, and concentrated to give the desired product G1(i) as a brown foam (0.35 g, 95%). Mass Spectrum: Calcd for C20H26N7OF2 (M+H): 418. Found: 418.

Quelle