Dimethylformamide → 2-Chloro-9-cyclohexyl-5-methyl-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one

HRID 2111306Notes

Reaction equation

HRID 2111306 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[NH:11][C:10](=[O:12])[CH2:9][CH2:8][N:7]([CH:13]3[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]3)[C:6]=2[N:19]=1.[C:20](=O)([O-])[O-].[Cs+].[Cs+].IC.CN(C)C=O>O>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[N:11]([CH3:20])[C:10](=[O:12])[CH2:9][CH2:8][N:7]([CH:13]3[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]3)[C:6]=2[N:19]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 866175922-Chloro-9-cyclohexyl-5,7,8,9-tetrahydropyrimido[4,5-b][1,4]diazepin-6-one

Product 1

HCID 714750712-Chloro-9-cyclohexyl-5-methyl-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.12 g (0.00042 mole) of 2-chloro-9-cyclohexyl-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one (VI-20), 0.469 g (0.00144 mole) of cesium carbonate, 0.135 g (0.00096 mole) of iodomethane and 1 mL of dimethylformamide was stirred overnight at ambient temperature and then diluted with 5 mL of water. The mixture was stirred for 15 minutes and the solid was collected by filtration to give 2-chloro-9-cyclohexyl-5-methyl-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one (VII-20) which was used without further purification.

Workup

  1. stirringThe mixture was stirred for 15 minutes
  2. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-b9c6b14b5bda4cd2b3d1185e4d91b86a
Source dataset
uspto-grants-2009_04
Patent number
US07517873B2

Reaction notes

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