Water → 1-Methyl-2-oxo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine-7-carboxylic acid ethyl ester

HRID 2096759Notes

Reaction equation

HRID 2096759 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:16]=[N:15][C:9]2[O:10][CH2:11][C:12](=[O:14])[NH:13][C:8]=2[CH:7]=1)=[O:5])[CH3:2].[CH3:17]C([O-])(C)C.[K+].CI.O>CN(C)C(=O)C>[CH2:1]([O:3][C:4]([C:6]1[CH:16]=[N:15][C:9]2[O:10][CH2:11][C:12](=[O:14])[N:13]([CH3:17])[C:8]=2[CH:7]=1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 23665647Potassium tert-butoxideHCID 675460622-Oxo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine-7-carboxylic acid ethyl ester

Product 1

HCID 675470391-Methyl-2-oxo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine-7-carboxylic acid ethyl esterYield 58%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of 2-oxo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine-7-carboxylic acid ethyl ester (1.518 g) in N,N-dimethylacetamide (15 ml) were added KOtBu (0.843 g) and methyl iodide (1.067 g). The mixture was stirred at room temperature for 2 h. Water was added and the mixture was extracted with EtOAc. The organic phase was dried (MgSO4), filtered and concentrated to dryness. The product was purified by chromatography (SiO2, CH2Cl2/MeOH 1:0=>9:1) to give the title compound (0.936 g) as a brown solid.

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. dry with materialThe organic phase was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated to dryness
  5. customThe product was purified by chromatography (SiO2, CH2Cl2/MeOH 1:0=>9:1)

Sources & evidence

ORD record
ord-eefcafe6f7d942a7a563153a1181b66c
Source dataset
uspto-grants-2013_05
Patent number
US08450313B2

Reaction notes

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