Methyl iodide → HCID 86637513, compound

HRID 1676805Notes

Reaction equation

HRID 1676805 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[NH:11][C:10](=[O:12])[C:9]([F:14])([F:13])[CH2:8][N:7]([CH2:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:6]=2[N:23]=1.[C:24](=O)([O-])[O-].[Cs+].[Cs+].IC>CN(C)C=O>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[N:11]([CH3:24])[C:10](=[O:12])[C:9]([F:14])([F:13])[CH2:8][N:7]([CH2:15][CH2:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:6]=2[N:23]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 86637512HCID 86637512, compound

Product 1

HCID 86637513HCID 86637513, compoundYield 61.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.64 g (0.0019 mole) of 2-chloro-7,7-difluoro-9-phenethyl-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one (VI-275) in 15 mL of dimethylformamide was added 0.92 g (0.0029 mole) of cesium carbonate, followed by 0.35 mL (0.0057 mole) of iodomethane. After stirring four hours, the mixture filtered and then concentrated under reduced pressure. Ice water and dichloromethane were added. The mixture was extracted with dichloromethane twice. The combined organic layers were washed three times with sodium carbonate, three times with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give 0.41 g of 2-chloro-7,7-difluoro-5-methyl-9-phenethyl-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one (VII-275) as a yellow solid.

Workup

  1. filtrationthe mixture filtered
  2. concentrationconcentrated under reduced pressure
  3. additionIce water and dichloromethane were added
  4. extractionThe mixture was extracted with dichloromethane twice
  5. washThe combined organic layers were washed three times with sodium carbonate, three times with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-728d7fa732c34cf9b7a6f983870661c0
Source dataset
uspto-grants-2011_08
Patent number
US08003785B2

Reaction notes

Loading…