Reaction equation
Cl[C:2]1[CH:12]=[C:6]2[N:7]([CH3:11])[CH2:8][CH2:9][CH2:10][N:5]2[C:4](=[O:13])[N:3]=1.[OH:14][CH2:15][C:16]1[CH:17]=[CH:18][C:19]([O:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][N:26]=2)=[C:20]([CH:23]=1)[C:21]#[N:22].[H-].[Na+]>CN(C)C=O>[CH3:11][N:7]1[CH2:8][CH2:9][CH2:10][N:5]2[C:4](=[O:13])[N:3]=[C:2]([O:14][CH2:15][C:16]3[CH:17]=[CH:18][C:19]([O:24][C:25]4[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:32])[F:33])=[CH:27][N:26]=4)=[C:20]([CH:23]=3)[C:21]#[N:22])[CH:12]=[C:6]12Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
The title compound was prepared by a procedure similar to that described for E1 starting from 8-chloro-1-methyl-3,4-dihydro-1H-pyrimido[1,6-a]pyrimidin-6(2H)-one and 5-(hydroxymethyl)-2-5 ((5-(trifluoromethyl)pyridin-2-yl)oxy)benzonitrile. An exemplary process is shown as below: To a solution of 5-(hydroxymethyl)-2-((5-(trifluoromethyl)pyridin-2-yl)oxy)benzonitrile (0.108 mL, 0.601 mmol) in N,N-dimethylformamide (DMF) (5 mL) was added NaH (48.1 mg, 1.202 mmol) and stirred for 10 mins. Then 8-chloro-1-methyl-3,4-dihydro-1H-pyrimido[1,6-a]pyrimidin-6(2H)-one (80 mg, 0.401 mmol) was charged and stirred for 45 mins at rt. The resulting solution was 10 quenched by addition of 1 mL aq. NH4Cl and the solution was filtered. The resulting solution was submitted for MDAP to afford the desired product as a white solid.
Workup
- customThe title compound was prepared by a procedure similar to
- stirringstirred for 45 mins at rt
- customquenched by addition of 1 mL aq. NH4Cl
- filtrationthe solution was filtered
Sources & evidence
- ORD record
- ord-78e117bd89b24d3ea0196cf7218b9e19
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09273054B2
Linked notes
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