Реакция #166365

Уравнение реакции

compound 4

9-Cyclopentyl-9H-pyrido[4′,3′:4,5]pyrrolo[2,3-d]pyrimidin-2-amine

compound 247

1-(6-chloro-3-pyridinyl)-4-(2-(((1,1-dimethylethyl)(dimethyl)silyl)oxy)ethyl)-piperazine

sodium t-butoxide

4,5-bis(diphenylphosphino)-9,9-dimethyl-9H-xanthene

→

compound 296

Выход 25.0%

N-(5-(4-(2-((tert-butyl(dimethyl)silyl)oxy)ethyl)-1-piperazinyl)-2-pyridinyl)-9-cyclopentyl-9H-pyrido[4′,3′:4,5]pyrrolo[2,3-d]pyrimidin-2-amine

Выход 25.0%

Растворители

dioxane

Условия реакции

Обработка

1. 1
   ДругоеA 10 mL reaction vessel
2. 2
   ДругоеThe reaction was purged with argon
3. 3
   ДругоеThe solvent was removed in vacuo and silica gel chromatography (
4. 4
   Промывкаgradient elution hexanes+2.5%/0-100% ethyl acetate+2.5% TEA

Методика

A 10 mL reaction vessel was charged with compound 4 (153 mg, 604 μmol), compound 247 (215 mg, 604 μmol), tris(dibenzylideneacetone)-dipalladium (0) (41.5 mg, 45.3 μmol), sodium t-butoxide (69.7 mg, 725 μmol), 4,5-bis(diphenylphosphino)-9,9-dimethyl-9H-xanthene (52.4 mg, 90.6 μmol), and dioxane (3 mL). The reaction was purged with argon and heated with microwave energy at 120° C. for 3.5 hours. The solvent was removed in vacuo and silica gel chromatography (gradient elution hexanes+2.5%/0-100% ethyl acetate+2.5% TEA, then ethyl acetate+2.5% TEA/0-5% methanol) afforded compound 296 as a yellow solid (85 mg, 25%).

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