Sodium hydride → 4-(2,6-Difluorobenzyl)-6-(1-methyl-2-butynyloxy)pyrimidine
Reaction equation
[H-].[Na+].[CH3:3][CH:4]([OH:8])[C:5]#[C:6][CH3:7].Cl[C:10]1[CH:15]=[C:14]([CH2:16][C:17]2[C:22]([F:23])=[CH:21][CH:20]=[CH:19][C:18]=2[F:24])[N:13]=[CH:12][N:11]=1.[Cl-].[NH4+]>O1CCCC1>[F:24][C:18]1[CH:19]=[CH:20][CH:21]=[C:22]([F:23])[C:17]=1[CH2:16][C:14]1[CH:15]=[C:10]([O:8][CH:4]([CH3:3])[C:5]#[C:6][CH3:7])[N:11]=[CH:12][N:13]=1Participants
Procedure
In 1 ml of tetrahydrofuran was suspended 0.04 g of sodium hydride (60% in oil), to which 0.2 ml of a tetrahydrofuran solution containing 0.06 g of 3-pentyn-2-ol was slowly added dropwise under stirring at room temperature. The mixture was stirred at room temperature for 20 minutes, and 0.4 ml of a tetrahydrofuran solution containing 0.15 g of 4-chloro-6-(2,6-difluorobenzyl)pyrimidine was slowly added dropwise at room temperature, followed by stirring for 3 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution and extracted three times with ethyl acetate. The organic layers were combined, washed with water, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give 0.24 g of 4-(2,6-difluorobenzyl)-6-(1-methyl-2-butynyloxy)pyrimidine (the present compound (147)).
Workup
- additionwas slowly added dropwise
- stirringThe mixture was stirred at room temperature for 20 minutes
- additionwas slowly added dropwise at room temperature
- stirringby stirring for 3 hours
- extractionextracted three times with ethyl acetate
- washwashed with water
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-0bd4c89b34dc4cd5b25a047b8dd4355c
- Source dataset
- uspto-grants-2007_11
- Patent number
- US07291730B2
Reaction notes
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