Methyl iodide → HCID 87617679, compound

HRID 2111323Notes

Reaction equation

HRID 2111323 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[NH:11][C:10](=[O:12])[CH:9]([CH3:13])[CH2:8][N:7]([CH2:14][CH2:15][CH:16]([CH3:18])[CH3:17])[C:6]=2[N:19]=1.I[CH3:21].[H-].[Na+]>CN(C)C=O>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[N:11]([CH3:21])[C:10](=[O:12])[CH:9]([CH3:13])[CH2:8][N:7]([CH2:14][CH2:15][CH:16]([CH3:18])[CH3:17])[C:6]=2[N:19]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 87619004HCID 87619004, compound

Product 1

HCID 87617679HCID 87617679, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 0.61 g, (0.00216 mole) of (rac)-2-chloro-7-methyl-9-(3-methyl-butyl)-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one (VI-27), 0.2 mL (0.00324 mole) of iodomethane and 7 mL of N,N-dimethyl-formamide at 0 degrees, was added 0.13 g (0.00324 mole) of sodium hydride, 60% dispersion in mineral oil. The mixture was stirred at 0 degree for 1.5 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 0.61 g of (rac)-2-chloro-5,7-dimethyl-9-(3-methyl-butyl)-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one (VII-27). HRMS (ES+) m/z Calcd for C14H21ClN4O+H [(M+H)+]: 297.1477. Found: 297.1476.

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-1c4c283227054627adc0a502c6b4ce6c
Source dataset
uspto-grants-2009_04
Patent number
US07517873B2

Reaction notes

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