반응 #162610

반응 방정식

hydrogen

4-(8-Oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-chloropyrimidin-2-ol

Sodium hydride

→

title compound

수율 85.1%

4-(8-Oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-isopropoxypyrimidin-2-ol

수율 85.1%

용매

2-propanol

반응 조건

후처리

1. 1
   기타resulting in a fine suspension
2. 2
   기타The vials were flushed with nitrogen
3. 3
   workup.ADDITIONSilica gel was added
4. 4
   기타the solvents were evaporated

실험 절차

4-(8-Oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-chloropyrimidin-2-ol (26, 460 mg, 1.903 mmol) was dissolved in 2-propanol (30 mL). The mixture was divided over two 20 mL microwave vials. Sodium hydride (305 mg, 7.61 mmol) was added (153 mg to each vial), resulting in a fine suspension. The vials were stirred at room temperature until no further formation of hydrogen gas was observed. The vials were flushed with nitrogen. The mixture was heated under microwave irradiation for 1 hour at 170° C. The 2 vials were combined and made acidic with 9 mL 1N HCl to pH˜3. Silica gel was added and the solvents were evaporated. Silica gel chromatography, using a gradient (0-20%) of MeOH in dichloromethane, gave the title compound (215 mg, 0.81 mmol, 43%) as a yellow foam.

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