Methyl iodide → HCID 87618406, compound

HRID 2111388Notes

Reaction equation

HRID 2111388 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][CH:15]3[CH2:19][CH2:18][CH2:17][CH2:16]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]([CH2:14][CH:15]3[CH2:16][CH2:17][CH2:18][CH2:19]3)[C:6]=2[N:20]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 87555541HCID 87555541, compound

Product 1

HCID 87618406HCID 87618406, compoundYield 95.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 1.10 g (0.00373 mole) of (rac)-2-chloro-9-cyclopentylmethyl-7-methyl-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one (VI-55), 0.35 mL (0.0056 mole) of iodomethane and 15 mL of N,N-dimethyl-formamide at 0 degrees, was added 0.22 g (0.0056 mole) of 60% oil dispersion of sodium hydride. The mixture was stirred at 0 degrees for 2 hours, then partitioned between ethyl acetate and water. The aqueous phase was extracted with ethyl acetate. The combined organic phases were washed 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 (100:0-60:60) to give 1.10 g of (rac)-2-chloro-9-cyclopentylmethyl-5,7-dimethyl-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one (VII-55) as white powder. HRMS (ES+) m/z Calcd for C15H21ClN4O+H [(M+H)+]: 309.1477. Found: 309.1476.

Workup

  1. custompartitioned between ethyl acetate and water
  2. extractionThe aqueous phase was extracted with ethyl acetate
  3. washThe combined organic phases were washed 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 (100:0-60:60)

Sources & evidence

ORD record
ord-4185630a9518494fb286ae9d1d160b9c
Source dataset
uspto-grants-2009_04
Patent number
US07517873B2

Reaction notes

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