Diethyl Ether → 2-[4-[(6-Bromohexyl)oxy]butyl]pyrimidine

HRID 982380Notes

Reaction equation

HRID 982380 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[CH2:7][CH2:8][CH2:9][CH2:10][OH:11].[Br:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]Br.[OH-].[Na+].CCOCC>O>[Br:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:11][CH2:10][CH2:9][CH2:8][CH2:7][C:2]1[N:3]=[CH:4][CH:5]=[CH:6][N:1]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 123681,6-DibromohexaneHCID 14798Sodium HydroxideHCID 19876764HCID 19876764, compound

Product 1

HCID 198767632-[4-[(6-Bromohexyl)oxy]butyl]pyrimidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-pyrimidinebutanol (1.31 g), 1,6-dibromohexane (5 ml), 50% aqueous sodium hydroxide solution (5 ml) and TAB (140 mg) was vigorously stirred under nitrogen at 23° for 20 h. Ether (25 ml) and water (20 ml) were added, the organic phase separated, washed with brine (20 ml), dried and evaporated in vacuo. The residue was purified by FCC. Elution with hexane and hexane-ether (9:1) followed by ether afforded the title compound as a colourless oil (1.67 g)

Workup

  1. customthe organic phase separated
  2. washwashed with brine (20 ml)
  3. customdried
  4. customevaporated in vacuo
  5. customThe residue was purified by FCC
  6. washElution with hexane and hexane-ether (9:1)

Sources & evidence

ORD record
ord-4a9e6bba0372456194590d2e0bdb4ea1
Source dataset
uspto-grants-1991_02
Patent number
US04996218

Reaction notes

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