Реакция #166366

Уравнение реакции

Tetrabutylammonium fluoride

Compound 296

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

Diethyl ether

→

compound 295

Выход 79.6%

2-(4-(6-((9-Cyclopentyl-9H-pyrido[4′,3′:4,5]pyrrolo[2,3-d]pyrimidin-2-yl)amino)-3-pyridinyl)-1-piperazinyl)ethanol

Выход 79.6%

Растворители

HCl

THF

THF

methanol

Условия реакции

Обработка

1. 1
   ДругоеThe solvent was removed in vacuo and silica gel chromatography (
2. 2
   Промывкаgradient elution hexanes+2.5%/0-100% ethyl acetate+2.5% TEA
3. 3
   Другоеethyl acetate+2.5% TEA/0-5% methanol) afforded a yellow solid
4. 4
   Другоеto precipitate the product, which
5. 5
   Фильтрацияwas filtered
6. 6
   Другоеdried in vacuo

Методика

Compound 296 (85.0 mg, 148 μmol) was dissolved in dry THF (3 mL).). Tetrabutylammonium fluoride, 1.0M in THF (1.00 mL, 1.00 mmol) was added and the reaction stirred at room temperature for 2 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 a yellow solid. This residue was taken up in methanol (3 mL) and 1M ethanolic HCl (1 mL). Diethyl ether (20 mL) was added to precipitate the product, which was filtered and dried in vacuo to give compound 295 as a yellow solid (54 mg, 79%). 1H NMR (500 MHz, DMSO-d6) δ 10.75-10.97 (m, 2 H) 9.70 (s, 2 H) 9.47 (s, 1 H) 8.74 (d, J=3.67 Hz, 2 H) 8.16 (d, J=2.45 Hz, 1 H) 7.99-8.10 (m, 1 H) 7.84-7.99 (m, 1 H) 5.30-5.52 (m, 1 H) 3.81-3.96 (m, 4 H) 3.62-3.72 (m, 2 H) 3.20-3.36 (m, 6 H) 2.39-2.49 (m, 2 H) 2.02-2.20 (m, 4 H) 0.88 (d, J=6.85 Hz, 2 H) ppm.

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