Methyl iodide → (Rac)-2-chloro-9-cyclopentyl-5,7-dimethyl-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one
Reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[NH:11][C:10](=[O:12])[CH:9]([CH3:13])[CH2:8][N:7]([CH:14]3[CH2:18][CH2:17][CH2:16][CH2:15]3)[C:6]=2[N:19]=1.[C:20](=O)([O-])[O-].[Cs+].[Cs+].CI>CN(C)C=O>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[N:11]([CH3:20])[C:10](=[O:12])[CH:9]([CH3:13])[CH2:8][N:7]([CH:14]3[CH2:18][CH2:17][CH2:16][CH2:15]3)[C:6]=2[N:19]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 46.72 g (0.166 mole) of (rac)-2-chloro-9-cyclopentyl-7-methyl-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one in 1000 mL of dimethylformamide was added 81.32 g (0.25 mole) of cesium carbonate, followed by 70.88 g (0.499 mole) of methyl iodide. After stirring four hours, the mixture filtered and then concentrated under reduced pressure. The residue was taken up in ethyl acetate and washed four times with water, once with brine and dried over anhydrous sodium sulfate. The mixture was filtered and then concentrated under reduced pressure to give 45 g of (rac)-2-chloro-9-cyclopentyl-5,7-dimethyl-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one (VII-1). This material was used subsequent steps without further purification.
Workup
- filtrationthe mixture filtered
- concentrationconcentrated under reduced pressure
- washwashed four times with water
- dry with materialonce with brine and dried over anhydrous sodium sulfate
- filtrationThe mixture was filtered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-d790976f2b44482c8f0ecbbc110c54b8
- Source dataset
- uspto-grants-2009_04
- Patent number
- US07517873B2
Reaction notes
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