Methyl iodide → HCID 87619625, compound

HRID 2111419Notes

Reaction equation

HRID 2111419 reaction equation
[CH2:1]([N:4]1[CH2:10][CH:9]([CH3:11])[C:8](=[O:12])[NH:7][C:6]2[CH:13]=[N:14][C:15]([Cl:17])=[N:16][C:5]1=2)[CH:2]=[CH2:3].I[CH3:19].[H-].[Na+]>CN(C)C=O>[CH2:1]([N:4]1[CH2:10][CH:9]([CH3:11])[C:8](=[O:12])[N:7]([CH3:19])[C:6]2[CH:13]=[N:14][C:15]([Cl:17])=[N:16][C:5]1=2)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 87619072HCID 87619072, compound

Product 1

HCID 87619625HCID 87619625, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 1.37 g (0.00542 mole) of (rac)-9-allyl-2-chloro-7-methyl-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one (VI-65), 0.51 mL (0.00813 mole) of iodomethane and 15 mL of N,N-dimethyl-formamide at 0 degrees, was added 0.33 g (0.00813 mole) of 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, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography, eluting with hexanes-ethyl acetate (100:0-60:40) to give 1.45 g of (rac)-9-allyl-2-chloro-5,7-dimethyl-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one (VII-65). HRMS (ES+) m/z Calcd for C12H15CIN4O+H [(M+H)+]: 267.1007. Found: 267.1007.

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. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography
  8. washeluting with hexanes-ethyl acetate (100:0-60:40)

Sources & evidence

ORD record
ord-4a9088b1f4a845589c02df7f160d3167
Source dataset
uspto-grants-2009_04
Patent number
US07517873B2

Reaction notes

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