Methyl iodide → HCID 19809374, compound

HRID 374084Notes

Reaction equation

HRID 374084 reaction equation
[Cl:1][C:2]1[C:11]2[NH:10][C:9](=[O:12])[CH2:8][O:7][C:6]=2[N:5]=[C:4]([CH2:13][CH3:14])[N:3]=1.[H-].[Na+].[CH3:17]I>CN(C)C=O.O>[Cl:1][C:2]1[C:11]2[N:10]([CH3:17])[C:9](=[O:12])[CH2:8][O:7][C:6]=2[N:5]=[C:4]([CH2:13][CH3:14])[N:3]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 19809380HCID 19809380, compound

Product 1

HCID 19809374HCID 19809374, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred suspension of 5 g (0.023 mole) of 4-chloro-6,7-dihydro-2-ethyl-5H-pyrimido[4,5-b][1,4]oxazin-6-one (prepared using the method of Melik-Ogandzhanyan, et al., Khimiya Geterotsiklicheskikh Soedinenii, 1985, 974) in 100 ml of N,N-dimethylformamide was added 0.75 g (0.025 mole) of 80% sodium hydride in oil. After ten minutes 3.5 g (0.025 mole) of methyl iodide was added. After two hours the solution was diluted with about 400 ml of water, and extracted thrice with 250 ml portions of chloroform. The extracts were washed with water, dried over magnesium sulfate, treated with decolorizing charcoal, and evaporated in vacuo. The resulting oil was triturated with a mixture of diethyl ether and hexanes to provide light green solid 4-chloro-6,7-dihydro-2-ethyl-5-methylpyrimido[4,5-b][1,4]oxazin-6-one.

Workup

  1. customprepared
  2. extractionextracted thrice with 250 ml portions of chloroform
  3. washThe extracts were washed with water
  4. dry with materialdried over magnesium sulfate
  5. additiontreated with decolorizing charcoal
  6. customevaporated in vacuo
  7. customThe resulting oil was triturated with a mixture of diethyl ether and hexanes

Sources & evidence

ORD record
ord-855a69bf47344006a0a483fcd11010bd
Source dataset
uspto-grants-1992_11
Patent number
US05166343

Reaction notes

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