Methyl iodide → HCID 87555943, compound

HRID 2111361Notes

Reaction equation

HRID 2111361 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]([CH:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[C:6]=2[N:20]=1.I[CH3:22].[H-].[Na+]>CN(C)C=O>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[N:11]([CH3:22])[C:10](=[O:12])[CH:9]([CH3:13])[CH2:8][N:7]([CH:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[C:6]=2[N:20]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 87617683HCID 87617683, compound

Product 1

HCID 87555943HCID 87555943, compoundYield 99.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a cooled mixture of 1.57 g (0.00529 mole) of (rac)-2-chloro-7-methyl-9-(tetrahydro-pyran-4-yl)-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one (VI-45), 0.49 mL (0.00794 mole) of iodomethane and 15 mL of N,N-dimethyl-formamide at 0 degrees was added 0.32 g (0.00794 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 and concentrated under reduced pressure. The residue was purified by silica gel chromatography, eluting with hexanes-ethyl acetate (100:0-60:40) to give 1.64 g of (rac)-2-chloro-5,7-dimethyl-9-(tetrahydro-pyran-4-yl)-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one (VII-45) as white powder. HRMS (ES+) m/z Calcd for C14H19CIN4O2+H [(M+H)+]: 311.1270. Found: 311.1269.

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-2fae73a8da82486ea6ee2d9ae00421ce
Source dataset
uspto-grants-2009_04
Patent number
US07517873B2

Reaction notes

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