Methyl iodide → 6-Bromo-1-methyl-1,4-dihydro-pyrido[2,3-d][1,3]oxazin-2-one

HRID 445724Notes

Reaction equation

HRID 445724 reaction equation
[Br:1][C:2]1[CH:12]=[N:11][C:5]2[NH:6][C:7](=[O:10])[O:8][CH2:9][C:4]=2[CH:3]=1.[H-].[Na+].I[CH3:16]>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[CH:12]=[N:11][C:5]2[N:6]([CH3:16])[C:7](=[O:10])[O:8][CH2:9][C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 159259906-bromo-1H,2H,4H-pyrido(2,3-d)(1,3)oxazin-2-one

Product 1

HCID 596197196-Bromo-1-methyl-1,4-dihydro-pyrido[2,3-d][1,3]oxazin-2-one

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6-bromo-1,4-dihydro-pyrido[2,3-d][1,3]oxazin-2-one (Stage 170.1.3, 0.707 mmol) in DMF (1.4 ml) was added 55% sodium hydride in oil (0.778 mmol). The RM was stirred for 5 min at rt then was added iodomethane (0.778 mmol) and the RM was stirred for 30 min at rt. The RM was diluted with EtOAc, washed with saturated NaHCO3, with brine (3×), dried over Na2SO4, filtered and evaporated. The residue was absorbed on silica gel and separated by flash chromatography (heptane/EtOAc 0% to 70%). The fractions containing product were evaporated together to give the title compound as a yellow solid. (HPLC: tR 2.64 min (Method A).

Workup

  1. stirringthe RM was stirred for 30 min at rt
  2. washwashed with saturated NaHCO3, with brine (3×)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was absorbed on silica gel
  7. customseparated by flash chromatography (heptane/EtOAc 0% to 70%)
  8. additionThe fractions containing product
  9. customwere evaporated together

Sources & evidence

ORD record
ord-82ea5e6779dc4a879124cd5e7fce1d0f
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

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