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

HRID 2111311Notes

Reaction equation

HRID 2111311 reaction equation
[CH2:1]([N:8]1[CH2:14][CH2:13][C:12](=[O:15])[NH:11][C:10]2[CH:16]=[N:17][C:18]([Cl:20])=[N:19][C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:21]N(C)C(=O)C.IC.[H-].[Na+]>O>[CH2:1]([N:8]1[CH2:14][CH2:13][C:12](=[O:15])[N:11]([CH3:21])[C:10]2[CH:16]=[N:17][C:18]([Cl:20])=[N:19][C:9]1=2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 31374DimethylacetamideHCID 581541759-Benzyl-2-chloro-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one

Product 1

HCID 581538799-Benzyl-2-chloro-5-methyl-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 0.144 g (0.0005 mole) of 9-benzyl-2-chloro-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one (VI-22), 1 mL of N,N-dimethylacetamide and 0.047 mL (0.00075 mole) of iodomethane at 0 degrees was added 0.03 g (0.00075 mole) of 60% sodium hydride in oil. The mixture was stirred at ambient temperature for 1 hour, then 20 mL of water was added. The precipitate was collected by filtration to give 0.134 g of 9-benzyl-2-chloro-5-methyl-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one (VII-22) as an yellow solid.

Workup

  1. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-f11a08a98f914d4085655e11c480c718
Source dataset
uspto-grants-2009_04
Patent number
US07517873B2

Reaction notes

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