Dimethylformamide → HCID 87555255, compound

HRID 2111303Notes

Reaction equation

HRID 2111303 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][CH2:17][CH2:16][CH2:15]3)[C:6]=2[N:20]=1.IC.[CH3:23]N(C)C=O.[H-].[Na+]>O>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[N:11]([CH3:23])[C:10](=[O:12])[CH:9]([CH3:13])[CH2:8][N:7]([CH:14]3[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)[C:6]=2[N:20]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 87555250HCID 87555250, compound

Product 1

HCID 87555255HCID 87555255, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To an ice cooled solution of 0.48 g (0.0016 mole) of (rac)-2-chloro-9-cyclohexyl-7-methyl-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one (VI-18), 0.2 mL (0.0032 mole) of iodomethane and 5 mL of dimethylformamide was added 0.13 g (0.0032 mole) of 60% oil dispersion of sodium hydride. The mixture was stirred at room temperature for 1 hour, then 100 mL of water was added and the mixture was extracted with twice with 100 mL of ethyl acetate. The organic layers were washed with 100 mL of brine, combined, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography, eluting with dichloromethane-ethyl acetate (85:15), followed by recrystallization from dichloromethane-hexanes to give 0.41 g of (rac)-2-chloro-9-cyclohexyl-5,7-dimethyl-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one (VII-19) as white needles.

Workup

  1. extractionthe mixture was extracted with twice with 100 mL of ethyl acetate
  2. washThe organic layers were washed with 100 mL of brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel chromatography
  7. washeluting with dichloromethane-ethyl acetate (85:15)
  8. customfollowed by recrystallization from dichloromethane-hexanes

Sources & evidence

ORD record
ord-f509cf0b68dc467685fc8fc608e6312a
Source dataset
uspto-grants-2009_04
Patent number
US07517873B2

Reaction notes

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