Sodium hydride → HCID 178458588, compound

HRID 75428Notes

Reaction equation

HRID 75428 reaction equation
[CH:1]12[O:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][N:3]([C:9]1[CH:14]=[C:13](Cl)[N:12]=[C:11]([OH:16])[N:10]=1)[CH2:2]2.[H-].[Na+].[H][H]>CC(O)C>[CH:1]12[O:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][N:3]([C:9]1[CH:14]=[C:13]([O:8][CH:5]([CH3:6])[CH3:4])[N:12]=[C:11]([OH:16])[N:10]=1)[CH2:2]2

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 178418361HCID 178418361, compoundHCID 178517808HCID 178517808, compound

Product 1

HCID 178458588HCID 178458588, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
170 °C

Procedure

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.

Workup

  1. customresulting in a fine suspension
  2. customThe vials were flushed with nitrogen
  3. additionSilica gel was added
  4. customthe solvents were evaporated

Sources & evidence

ORD record
ord-94123f55c6884976854bca51f0817e19
Source dataset
uspto-grants-2014_09
Patent number
US08835429B2

Reaction notes

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