Reaction equation
[H-].[Na+].[CH2:3]([OH:7])[C:4]#[C:5][CH3:6].Cl[C:9]1[C:14]([F:15])=[C:13]([N:16]2[CH2:21][C@H:20]([CH3:22])[CH2:19][C@H:18]([CH3:23])[CH2:17]2)[N:12]=[CH:11][N:10]=1.[Cl-].[NH4+]>O1CCCC1>[CH2:3]([O:7][C:9]1[C:14]([F:15])=[C:13]([N:16]2[CH2:21][C@H:20]([CH3:22])[CH2:19][C@H:18]([CH3:23])[CH2:17]2)[N:12]=[CH:11][N:10]=1)[C:4]#[C:5][CH3:6]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
0.10 g of sodium hydride (60% oil suspension) was suspended in 3 ml of tetrahydrofuran. 1 ml of tetrahydrofuran solution of 0.16 g of 2-butyn-1-ol was added dropwise therein, and the mixture was stirred for 10 minutes. Into the mixture was added dropwise 1 ml of tetrahydrofuran solution of 0.31 g of 4-chloro-6-(cis-3,5-dimethylpiperidino)-5-fluoropyrimidine and stirred for 6 hours at 60° C. Into the reaction mixture was added a saturated ammonium chloride aqueous solution, and the mixture was extracted with tert-butyl methyl ether three times. The organic layers were washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.32 g of 4-(2-butynyloxy)-5-fluoro-6-(cis-3,5-dimethylpiperidino)pyrimidine (hereinafter, referred to as Compound (29)).
Workup
- stirringstirred for 6 hours at 60° C
- extractionthe mixture was extracted with tert-butyl methyl ether three times
- washThe organic layers were washed with a saturated sodium chloride aqueous solution
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-bf62f21c27154816a6039d2c265a9305
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07732448B2
Linked notes
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