Methyl iodide → HCID 67282969, compound

HRID 1616127Notes

Reaction equation

HRID 1616127 reaction equation
[H-].[Na+].[CH3:3][C:4]1[NH:13][C:12](=[O:14])[C:11]2[C:6](=[CH:7][C:8]([C:15]([O:17][CH3:18])=[O:16])=[CH:9][CH:10]=2)[N:5]=1.[CH3:19]I>CN(C=O)C>[CH3:3][C:4]1[N:13]([CH3:19])[C:12](=[O:14])[C:11]2[C:6](=[CH:7][C:8]([C:15]([O:17][CH3:18])=[O:16])=[CH:9][CH:10]=2)[N:5]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 135890465methyl 2-methyl-4-oxo-3,4-dihydroquinazoline-7-carboxylate

Product 1

HCID 67282969HCID 67282969, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred suspension of sodium hydride (60% in mineral oil, 51 mg, 1.28 mmol) in DMF (5 mL) under an atmosphere of nitrogen was added methyl 2-methyl-4-oxo-3,4-dihydroquinazoline-7-carboxylate (0.14 g, 0.64 mmol) in DMF (2 mL) dropwise. Methyl iodide (80 μL, 1.28 mmol) was then added to the mixture and the resulting solution was stirred at rt overnight. The reaction was quenched with water and extracted with DCM (2×). The combined organic phases were then washed with water, and brine, dried over anhydrous Na2SO4, filtered and concentrated to afford methyl 2,3-dimethyl-4-oxo-3,4-dihydroquinazoline-7-carboxylate (70 mg, 50%). LC-MS: (FA) ES+ 233.

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with DCM (2×)
  3. washThe combined organic phases were then washed with water, and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6ca2a2d801e447d59d87055b2a22a8a9
Source dataset
uspto-grants-2014_07
Patent number
US08765773B2

Reaction notes

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