Sodium hydride → HCID 67391482, compound

HRID 2359008Notes

Reaction equation

HRID 2359008 reaction equation
[H-].[Na+].[O:3]1[CH2:8][C:7](=[O:9])[NH:6][C:5]2[N:10]=[CH:11][CH:12]=[CH:13][C:4]1=2.[CH3:14][Si:15]([CH3:22])([CH3:21])[CH2:16][CH2:17][O:18][CH2:19]Cl>CN(C=O)C>[CH3:14][Si:15]([CH3:22])([CH3:21])[CH2:16][CH2:17][O:18][CH2:19][N:6]1[C:7](=[O:9])[CH2:8][O:3][C:4]2[CH:13]=[CH:12][CH:11]=[N:10][C:5]1=2

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 884992H-pyrido(3,2-b)-1,4-oxazin-3(4H)-oneHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl ether

Product 1

HCID 67391482HCID 67391482, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% dispersion in mineral oil; 0.48 g, 12 mmol) is added in portions to a solution of 2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one (1.50 g, 10 mmol) in DMF (20 mL) at 0° C. and the mixture is stirred for 1 h. 2-(Trimethylsilyl)ethoxymethylchloride (2.1 mL, 12 mmol) is added slowly dropwise and the mixture is then stirred at rt for 1 h. The reaction is quenched by pouring into ice-water and the mixture is then extracted with CH2Cl2 (×3). The combined organic extracts are washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The crude product is purified by silica gel chromatography (gradient elution with hexanes-EtOAc) to afford the title compound.

Workup

  1. stirringthe mixture is then stirred at rt for 1 h
  2. customThe reaction is quenched
  3. additionby pouring into ice-water
  4. extractionthe mixture is then extracted with CH2Cl2 (×3)
  5. washThe combined organic extracts are washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude product is purified by silica gel chromatography (gradient elution with hexanes-EtOAc)

Sources & evidence

ORD record
ord-51b69d10199c4de3a411cd31252f66bd
Source dataset
uspto-grants-2014_04
Patent number
US08685965B2

Reaction notes

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