Methyl iodide → 2-Chloro-9-cyclopentyl-7,7-dichloro-5-methyl-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one

HRID 1676838Notes

Reaction equation

HRID 1676838 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[NH:11][C:10](=[O:12])[C:9]([Cl:14])([Cl:13])[CH2:8][N:7]([CH:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)[C:6]=2[N:20]=1.[C:21](=O)([O-])[O-].[Cs+].[Cs+].IC>CN(C)C=O>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[N:11]([CH3:21])[C:10](=[O:12])[C:9]([Cl:14])([Cl:13])[CH2:8][N:7]([CH:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)[C:6]=2[N:20]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 866375262-Chloro-9-cyclopentyl-7,7-dichloro-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one

Product 1

HCID 866375272-Chloro-9-cyclopentyl-7,7-dichloro-5-methyl-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-oneYield 74.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.60 g (0.0018 mole) of 2-chloro-9-cyclopentyl-7,7-dichloro-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one (VI-298) in 12 mL of dimethylformamide was added 0.88 g (0.0027 mole) of cesium carbonate, followed by 0.34 mL (0.0054 mole) of iodomethane. After stirring four hours, the mixture was filtered and then concentrated under reduced pressure. Ice water was added to the residue and the resulting solid was collected by filtration, washed with water and dried under vacuum to give 0.47 g of 2-chloro-9-cyclopentyl-7,7-dichloro-5-methyl-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one (VII-298) as a white solid.

Workup

  1. filtrationthe mixture was filtered
  2. concentrationconcentrated under reduced pressure
  3. additionIce water was added to the residue
  4. filtrationthe resulting solid was collected by filtration
  5. washwashed with water
  6. customdried under vacuum

Sources & evidence

ORD record
ord-5e92b551725243c19caf11f00580d922
Source dataset
uspto-grants-2011_08
Patent number
US08003785B2

Reaction notes

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