1,6-Dibromohexane → 5-[6-[(6-Bromohexyl)oxy]hexyl]pyrimidine

HRID 982384Notes

Reaction equation

HRID 982384 reaction equation
[N:1]1[CH:6]=[C:5]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:13])[CH:4]=[N:3][CH:2]=1.[OH-].[Na+].[Br:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]Br>O.CCOCC>[Br:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][O:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:5]1[CH:6]=[N:1][CH:2]=[N:3][CH:4]=1

Participants

6

Reactant 3

HCID 123681,6-DibromohexaneHCID 14798Sodium HydroxideHCID 135575446-(Pyrimidin-5-yl)hexan-1-ol

Product 1

HCID 198767545-[6-[(6-Bromohexyl)oxy]hexyl]pyrimidine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 5-pyrimidinehexanol (1.82 g), 50% sodium hydroxide (6 ml), 1,6-dibromohexane (6 ml) and TAB (150 mg) was vigorously stirred at room temperature for 30 h then diluted with water (20 ml) and ether (25 ml). The organic phase was dried and evaporated in vacuo. The residue was purified by FCC eluting with hexane followed by hexane-ether (1:1) and ether, to give the title compound as a colourless liquid (2.21 g), t.l.c. (ether) Rf 0.35.

Workup

  1. customThe organic phase was dried
  2. customevaporated in vacuo
  3. customThe residue was purified by FCC
  4. washeluting with hexane

Sources & evidence

ORD record
ord-385cdbf4a8c340ed90403123ae3429cc
Source dataset
uspto-grants-1991_02
Patent number
US04996218

Reaction notes

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