Sodium hydride → HCID 66750665, compound

HRID 75417

Reaction equation

HRID 75417 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][CH:9]=2)[N:5]=[C:4]([N:17]2[CH2:23][CH:22]3[O:24][CH:19]([CH2:20][CH2:21]3)[CH2:18]2)[CH:3]=1.[H-].[Na+].[H][H]>CC(O)C>[CH:22]([O:24][C:2]1[CH:3]=[C:4]([N:17]2[CH2:23][CH:22]3[O:24][CH:19]([CH2:20][CH2:21]3)[CH2:18]2)[N:5]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=2)[N:7]=1)([CH3:23])[CH3:21]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 866658843-[6-Chloro-2-(4-nitro-phenyl)-pyrimidin-4-yl]-8-oxa-3-aza-bicyclo[3.2.1]octaneHCID 178418361HCID 178418361, compound

Product 1

HCID 66750665HCID 66750665, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
140 °C

Procedure

In a 2-5 mL microwave vial was placed 3-(6-chloro-2-(4-nitrophenyl)pyrimidin-4-yl)-8-oxa-3-azabicyclo[3.2.1]octane (13, 70 mg, 0.202 mmol) in 2-propanol (4 mL) to give a yellow suspension. Sodium hydride (60% in oil, 32.3 mg, 0.807 mmol) was added and the mixture was stirred until no further formation of hydrogen gas was observed. The reaction was heated under microwave irradiation at 140° C. for 30 min to give a bright orange suspension. Work-up: the solvents were evaporated. The residue was dissolved in dichloromethane and washed with sat NaHCO3. The organic phase was dried over MgSO4, filtered and concentrated to give the title compound in a quantitative yield.

Workup

  1. customto give a yellow suspension
  2. customto give a bright orange suspension
  3. customthe solvents were evaporated
  4. dissolutionThe residue was dissolved in dichloromethane
  5. washwashed
  6. dry with materialThe organic phase was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-b13fb660e2a540fdbacf5424beaf4f4a
Source dataset
uspto-grants-2014_09
Patent number
US08835429B2

Linked notes

Loading…