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

HRID 75066Notes

Reaction equation

HRID 75066 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

5

Reactant 3

HCID 3283Diethyl EtherHCID 10796Cesium carbonateHCID 135585902Phenol, 4-(5-decyl-2-pyrimidinyl)-

Product 1

HCID 198347485-Decyl-2-(4-(hept-6-enyloxy)phenyl)pyrimidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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).

Workup

  1. customA vinyl-terminated phenyl pyrimidine side group
  2. customwas synthesized from 4-(5-decylpyrimidin-2-yl)phenol for siloxane coupling to 1,2 polybutadiene using standard ether chemistry
  3. extractionThe reaction mixture was extracted three times with 50 mL of dichloromethane
  4. washThe organic extracts were washed three times with water
  5. dry with materialdried with MgSO4
  6. customThe crude product was recrystallized in hot 95% ethanol

Sources & evidence

ORD record
ord-df57ae57b9ea48cab9c811ab6917bdc9
Source dataset
uspto-grants-2014_09
Patent number
US08834742B2

Reaction notes

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