Methyl iodide → HCID 68905377, compound

HRID 2111422Notes

Reaction equation

HRID 2111422 reaction equation
[CH3:1][O:2][C:3](=[O:33])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[N:12]=[CH:13][C:14]3[N:20]([CH3:21])[C:19](=[O:22])[CH:18]([CH3:23])[CH2:17][N:16]([CH:24]4[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]4)[C:15]=3[N:30]=2)=[C:6]([O:31][CH3:32])[CH:5]=1.I[CH3:35].[H-].[Na+]>CN(C)C=O>[CH3:1][O:2][C:3](=[O:33])[C:4]1[CH:9]=[CH:8][C:7]([N:10]([C:11]2[N:12]=[CH:13][C:14]3[N:20]([CH3:21])[C:19](=[O:22])[CH:18]([CH3:23])[CH2:17][N:16]([CH:24]4[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]4)[C:15]=3[N:30]=2)[CH3:35])=[C:6]([O:31][CH3:32])[CH:5]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 68904178HCID 68904178, compound

Product 1

HCID 68905377HCID 68905377, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 0.170 g (0.00037 mole) of (rac)-4-(9-cyclohexyl-5,7-dimethyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-yl amino)-3-methoxy-benzoic acid methyl ester, 0.35 mL (0.00056 mole) of iodomethane and 10 mL of N,N-dimethylformamide at 0 degrees, was added 0.024 g of sodium hydride (60% dispersion in mineral oil). 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, and 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 chromatography, eluting with hexanes-ethyl acetate (30:70) to give 0.170 g of (rac)-4-[(9-cyclohexyl-5,7-dimethyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-yl)-methyl-amino]-3-methoxy-benzoic acid methyl ester as white powder.

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 chromatography
  8. washeluting with hexanes-ethyl acetate (30:70)

Sources & evidence

ORD record
ord-cbc0a60522414894b6c507f19513b9ef
Source dataset
uspto-grants-2009_04
Patent number
US07517873B2

Reaction notes

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