Propargyl alcohol → 4-Methyl-6-propargyloxy-2-(6-n-propyl-2-pyridinyl)pyrimidine
Reaction equation
C(O)C#C.[H-].[Na+].[C:7]([O-:11])(=O)[C:8]#[CH:9].[Na+].Cl[C:14]1[CH:19]=[C:18]([CH3:20])[N:17]=[C:16]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([CH2:27][CH2:28][CH3:29])[N:22]=2)[N:15]=1>O1CCCC1.C(Cl)(Cl)Cl>[CH3:20][C:18]1[CH:19]=[C:14]([O:11][CH2:7][C:8]#[CH:9])[N:15]=[C:16]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([CH2:27][CH2:28][CH3:29])[N:22]=2)[N:17]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of propargyl alcohol (0.82 g) in anhydrous tetrahydrofuran (80 ml) was added 60 % oily sodium hydride (0.58 g) to prepare sodium propargylate. To this solution was added at room temperature 4-chloro-6-methyl-2-(6-n-propyl-2-pyridinyl)pyrimidine (3 g). The mixture was stirred for one hour and then concentrated under reduced pressure. To the redidue obtained was added chloroform (100 ml). The mixture was washed twice with water (30 ml each) and dried over anhydrous magnesium sulfate, followed by concentration under reduced pressure. The crystalline residue obtained was washed with hexane to obtain 4-methyl-6-propargyloxy-2-(6-n-propyl-2-pyridinyl)pyrimidine (2.7 g, yield: 83 %).
Workup
- concentrationconcentrated under reduced pressure
- customTo the redidue obtained
- washThe mixture was washed twice with water (30 ml each)
- dry with materialdried over anhydrous magnesium sulfate
- concentrationfollowed by concentration under reduced pressure
- customThe crystalline residue obtained
- washwas washed with hexane
Sources & evidence
- ORD record
- ord-87d822a5db91496b9970effadab1d49f
- Source dataset
- uspto-grants-1988_06
- Patent number
- US04752608
Reaction notes
Loading…