Methyl iodide → HCID 86637516, compound

HRID 1676811Notes

Reaction equation

HRID 1676811 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][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:6]=2[N:24]=1.[C:25](=O)([O-])[O-].[Cs+].[Cs+].IC>CN(C)C=O>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[N:11]([CH3:25])[C:10](=[O:12])[C:9]([F:14])([F:13])[CH2:8][N:7]([CH2:15][CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:6]=2[N:24]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 86637514HCID 86637514, compound

Product 1

HCID 86637516HCID 86637516, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1.0 g (0.0028 mole) of 2-chloro-7,7-difluoro-9-(3-phenyl-propyl)-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one (VI-281) in 20 mL of dimethylformamide was added 1.4 g (0.0042 mole) of cesium carbonate, followed by 0.53 mL (0.0084 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 0.98 g of 2-chloro-7,7-difluoro-5-methyl-9-(3-phenyl-propyl)-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one (VII-281) as a yellow oil.

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-2afd98b485dc40b3af9bc1986b782378
Source dataset
uspto-grants-2011_08
Patent number
US08003785B2

Reaction notes

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