Methyl iodide → HCID 87619633, compound

HRID 2111345Notes

Reaction equation

HRID 2111345 reaction equation
[CH2:1]([N:8]1[CH2:14][CH:13]([CH3:15])[C:12](=[O:16])[NH:11][C:10]2[CH:17]=[N:18][C:19]([Cl:21])=[N:20][C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.I[CH3:23].[H-].[Na+]>CN(C)C=O>[CH2:1]([N:8]1[CH2:14][CH:13]([CH3:15])[C:12](=[O:16])[N:11]([CH3:23])[C:10]2[CH:17]=[N:18][C:19]([Cl:21])=[N:20][C:9]1=2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 87618405HCID 87618405, compound

Product 1

HCID 87619633HCID 87619633, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To an ice cooled mixture of 1.38 g (0.0046 mole) of (rac)-9-benzyl-2-chloro-7-methyl-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one (VI-42), 0.43 mL (0.0068 mole) of iodomethane and 15 mL of dimethylformamide was added 0.27 g (0.0068 mole) of a 60% oil dispersion of sodium hydride. The mixture was stirred at 0 degrees for 2 hours and then partitioned between ethyl acetate and water. The aqueous phase was extracted with ethyl acetate. The combined organic phases were washed successively with water and brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography eluting with hexanes-ethyl acetate (100:0-60:40) to give 1.36 g of (rac)-9-benzyl-2-chloro-5,7-dimethyl-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one as white powder (VII-42).

Workup

  1. custompartitioned between ethyl acetate and water
  2. extractionThe aqueous phase was extracted with ethyl acetate
  3. washThe combined organic phases were washed successively with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel chromatography
  7. washeluting with hexanes-ethyl acetate (100:0-60:40)

Sources & evidence

ORD record
ord-f2807e60194542aebb6ca5d1b45382ce
Source dataset
uspto-grants-2009_04
Patent number
US07517873B2

Reaction notes

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