Sodium hydride → 4-(2-Butynyloxy)-6-(3,3-dimethylpiperidino)-5-fluoropyrimidine
Reaction equation
[H-].[Na+].Cl.[CH3:4][C:5]1([CH3:11])[CH2:10][CH2:9][CH2:8][NH:7][CH2:6]1.[CH2:12]([O:16][C:17]1[C:22]([F:23])=[C:21](Cl)[N:20]=[CH:19][N:18]=1)[C:13]#[C:14][CH3:15].[Cl-].[NH4+]>O1CCCC1>[CH2:12]([O:16][C:17]1[C:22]([F:23])=[C:21]([N:7]2[CH2:8][CH2:9][CH2:10][C:5]([CH3:11])([CH3:4])[CH2:6]2)[N:20]=[CH:19][N:18]=1)[C:13]#[C:14][CH3:15]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
0.12 g of sodium hydride (60% oil suspension) was suspended in 2 ml of tetrahydrofuran. 0.18 g of 3,3-dimethylpiperidine hydrochloride and 0.20 g of 4-(2-butynyloxy)-6-chloro-5-fluoropyrimidine were added therein, and the mixture was stirred for 1 hour at 60%. After the reaction mixture was cooled to near room temperature, a saturated ammonium chloride aqueous solution was added therein, 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 0.05 g of 4-(2-butynyloxy)-6-(3,3-dimethylpiperidino)-5-fluoropyrimidine (hereinafter, referred to as Compound (32)).
Workup
- 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-dfc33ca296da48a89049c13aa8196bba
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07732448B2
Reaction notes
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