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Methyl iodide → 2-Chloro-7,7-difluoro-5-methyl-9-(2-thiophen-2-yl-ethyl)-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one

HRID 1676802
Notes
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Reaction equation

HRID 1676802 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[S:18][CH:19]=[CH:20][CH:21]=3)[C:6]=2[N:22]=1.[C:23](=O)([O-])[O-].[Cs+].[Cs+].IC>CN(C)C=O>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[N:11]([CH3:23])[C:10](=[O:12])[C:9]([F:13])([F:14])[CH2:8][N:7]([CH2:15][CH2:16][C:17]3[S:18][CH:19]=[CH:20][CH:21]=3)[C:6]=2[N:22]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 866375092-Chloro-7,7-difluoro-9-(2-thiophen-2-yl-ethyl)-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one

Product 1

HCID 866375102-Chloro-7,7-difluoro-5-methyl-9-(2-thiophen-2-yl-ethyl)-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-oneYield 102.2%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

To a solution of 0.51 g (0.0015 mole) of 2-chloro-7,7-difluoro-9-(2-thiophen-2-yl-ethyl)-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one (VI-269) in 12 mL of dimethylformamide was added 0.58 g (0.0023 mole) of cesium carbonate, followed by 0.28 mL (0.0045 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 0.55 g of 2-chloro-7,7-difluoro-5-methyl-9-(2-thiophen-2-yl-ethyl)-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one (VII-269) as a sticky 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-94c59bf6421d4ce8978f013aa3daba56
Source dataset
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08003785B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes