반응 #168020

반응 방정식

sodium carbonate

(R)-6-benzyl-2-chloro-4-(4-methoxy-3,3-dimethylpiperidin-1-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine

3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-indazole

→

title compound

(R)-6-Benzyl-2-(3,5-dimethyl-1-tosyl-1H-indazol-4-yl)-4-(4-methoxy-3,3-dimethylpiperidin-1-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine

용매

1,4-dioxane

EtOAc

water

반응 조건

후처리

1. 1
   온도to cool to rt
2. 2
   workup.ADDITIONThe layers were mixed
3. 3
   기타separated
4. 4
   세척The organic layer was washed with water
5. 5
   건조The separated organic layer was then dried over sodium sulfate
6. 6
   여과filtered
7. 7
   농축concentrated
8. 8
   기타The residue was then purified via FCC (0-70% EtOAc/heptane)

실험 절차

To a solution of (R)-6-benzyl-2-chloro-4-(4-methoxy-3,3-dimethylpiperidin-1-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine (5.04 g, 12.6 mmol) in 1,4-dioxane (100 mL) was added 3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-indazole, Example 3, (6.16 g, 12.6 mmol), Pd(Ph3P)4 (2.18 g, 1.89 mmol) and a 2 M solution of sodium carbonate (18.9 mL, 37.7 mmol). The reaction mixture was heated at 100° C. under a nitrogen atmosphere for 16 h. The reaction mixture was then allowed to cool to rt and was diluted with EtOAc and water. The layers were mixed and then separated. The organic layer was washed with water and then brine. The separated organic layer was then dried over sodium sulfate, filtered and concentrated. The residue was then purified via FCC (0-70% EtOAc/heptane) to give the title compound. MS (ESI+) m/z 665.6 (M+H)+.

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