Diethyl Ether → 5-Decyl-2-(4-(hept-6-enyloxy)phenyl)pyrimidine

Reaction equation

[CH2:1]([C:11]1[CH:12]=[N:13][C:14]([C:17]2[CH:22]=[CH:21][C:20](O)=[CH:19][CH:18]=2)=[N:15][CH:16]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[C:24]([O-:27])([O-])=O.[Cs+].[Cs+].CCO[CH2:33][CH3:34]>CN(C)C=O>[CH2:1]([C:11]1[CH:12]=[N:13][C:14]([C:17]2[CH:22]=[CH:21][C:20]([O:27][CH2:24][CH2:11][CH2:1][CH2:2][CH2:3][CH:33]=[CH2:34])=[CH:19][CH:18]=2)=[N:15][CH:16]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

Procedure

A vinyl-terminated phenyl pyrimidine side group was synthesized from 4-(5-decylpyrimidin-2-yl)phenol for siloxane coupling to 1,2 polybutadiene using standard ether chemistry as follows: 4-(5-decylpyrimidin-2-yl)phenol (1.93 grams, 6.15 mmols), a bromoalkene (7-bromohept-1-ene, 1.22 mL, 8 mmol) and oven-dried Cs2CO3 (2.56 grams, 8 mmol) were stirred at room temperature in 40 mL of dimethyl formamide overnight, resulting in near-quantitative conversion to the ether (Scheme 6), as monitored by thin layer chromatography. The reaction mixture was extracted three times with 50 mL of dichloromethane. The organic extracts were washed three times with water and dried with MgSO4. The crude product was recrystallized in hot 95% ethanol, resulting in analytically pure white crystals of 5-decyl-2-(4-(hept-6-enyloxy)phenyl)pyrimidine, enyloxy)phenyl)pyrimidine, or C7PPC10V, (1.69 g, 66.0% overall yield).