Acetonitrile → 6-(2-Pyrimidinyl)-5-hexyn-1-ol

HRID 1886009Notes

Reaction equation

HRID 1886009 reaction equation
Br[C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[CH2:8]([OH:14])[CH2:9][CH2:10][CH2:11][C:12]#[CH:13].C1(NC2CCCCC2)CCCCC1.C(#N)C>[Cu]I.CCOCC>[N:3]1[CH:4]=[CH:5][CH:6]=[N:7][C:2]=1[C:13]#[C:12][CH2:11][CH2:10][CH2:9][CH2:8][OH:14]

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 7582DicyclohexylamineHCID 702345-Hexyn-1-olHCID 783452-Bromopyrimidine

Product 1

HCID 198767486-(2-Pyrimidinyl)-5-hexyn-1-olYield 83.1%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2-bromopyrimidine (3.96 g), 5-hexynol (2.44 g), dicylohexylamine (4 g), BTPC (250 mg), copper (I) iodide (25 mg) and acetonitrile (40 ml) was stirred at ambient temperature under nitrogen for 1 h (temp. rose to ~45°). Ether (120 ml) was added, the mixture was filtered and the filtrate was evaporated in vacuo to an oil which was purified by FCC. Elution with ether followed by System C (17:3) gave the title compound as a pale yellow oil (3.64 g), t.l.c. (System C 17:3) Rf 0.34.

Workup

  1. filtrationthe mixture was filtered
  2. customthe filtrate was evaporated in vacuo to an oil which
  3. customwas purified by FCC
  4. washElution with ether

Sources & evidence

ORD record
ord-98e34badcb7c415daa2cc8478faa0e26
Source dataset
uspto-grants-1992_09
Patent number
US05149698

Reaction notes

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