Methyl iodide → HCID 86637519, compound

HRID 1676820Notes

Reaction equation

HRID 1676820 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]([C@@H:15]3[CH2:17][C@H:16]3[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]([C@@H:15]3[CH2:17][C@H:16]3[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:6]=2[N:24]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 86637518HCID 86637518, compound

Product 1

HCID 86637519HCID 86637519, compoundYield 89.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 7.0 g (0.020 mole) of 2-chloro-7,7-difluoro-9-(trans-2-phenyl-cyclopropyl)-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one (VI-287) in 140 mL of dimethylformamide was added 9.7 g (0.030 mole) of cesium carbonate, followed by 3.7 mL (0.060 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 6.5 g of 2-chloro-7,7-difluoro-5-methyl-9-(trans-2-phenyl-cyclopropyl)-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one (VII-287) 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-8967a2e5275c4241aee00be0765b32c6
Source dataset
uspto-grants-2011_08
Patent number
US08003785B2

Reaction notes

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