反应 #166351

反应方程式

diethyl ether

Tetrabutylammonium fluoride

Compound 276

9-Cyclopentyl-2-((5-((3R)-3-(tert-butyldimethylsilyloxy)pyrrolidin-1-yl)-2-pyridinyl)amino)-8-methyl-8,9-dihydro-7H-pyrido[3′,2′:4,5]pyrrolo[2,3-d]-pyrimidin-7-one

NaHCO3

→

compound 275

收率 50.0%

9-Cyclopentyl-2-((5-((3R)-3-hydroxy-1-pyrrolidinyl)-2-pyridinyl)amino)-8-methyl-8,9-dihydro-7H-pyrido[3′,2′:4,5]pyrrolo[2,3-d]pyrimidin-7-one

收率 50.0%

溶剂

methanol

methanol

THF

THF

反应条件

后处理

1. 1
   其他The solvent was evaporated
2. 2
   其他to give an orange oil
3. 3
   洗涤Preparative reverse phase HPLC (gradient elution 0.1% TFA in water/10-70% acetonitrile)
4. 4
   其他afforded a yellow solid
5. 5
   萃取extracted with dichloromethane+10% methanol (3×30 mL)
6. 6
   干燥The combined organics were dried (MgSO4)
7. 7
   其他evaporated
8. 8
   其他to give a yellow solid
9. 9
   其他to precipitate the product, which
10. 10
    洗涤was washed with ether
11. 11
    其他dried in vacuo

实验过程

Compound 276 (53.0 mg, 94.7 μmol) was dissolved in THF (2 mL).). Tetrabutylammonium fluoride, 1.0M in THF (0.500 mL, 500 μmol) was added and the reaction was stirred at room temperature for 4.5 hours. The solvent was evaporated to give an orange oil. Preparative reverse phase HPLC (gradient elution 0.1% TFA in water/10-70% acetonitrile) afforded a yellow solid. This residue was added to aqueous NaHCO3 (saturated, 10 mL) and extracted with dichloromethane+10% methanol (3×30 mL). The combined organics were dried (MgSO4) and evaporated to give a yellow solid. This product was taken up in methanol (2 mL) and 1 mL methanol (saturated at room temperature with HCl) was added. 20 mL diethyl ether was added to precipitate the product, which was washed with ether and dried in vacuo to give compound 275 as yellow solid (21 mg, 50%). 1H NMR (500 MHz, DMSO-d6) δ 9.21 (s, 2 H) 8.56 (d, J=8.56 Hz, 2 H) 7.63 (d, J=2.69 Hz, 4 H) 7.44-7.57 (m, 2 H) 6.87 (d, J=8.56 Hz, 2 H) 5.43 (quin, J=8.62 Hz, 1 H) 4.47 (br. s., 1 H) 4.00 (s, 3 H) 3.09-3.21 (m, 1H) 2.00-2.22 (m, 5 H) 1.90-2.04 (m, 1 H) 1.66-1.85 (m, 2 H) ppm.

来源