Dicyclohexylamine → 6-(Pyrimidin-5-YL)hex-5-YN-1-OL

HRID 982376Notes

Reaction equation

HRID 982376 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[N:6][CH:7]=1.[CH2:8]([OH:14])[CH2:9][CH2:10][CH2:11][C:12]#[CH:13].C1(NC2CCCCC2)CCCCC1>[Cu]I.C(#N)C>[N:4]1[CH:3]=[C:2]([C:13]#[C:12][CH2:11][CH2:10][CH2:9][CH2:8][OH:14])[CH:7]=[N:6][CH:5]=1

Participants

6

Reactant 3

HCID 7582DicyclohexylamineHCID 702345-Hexyn-1-olHCID 783445-Bromopyrimidine

Product 1

HCID 139997526-(Pyrimidin-5-YL)hex-5-YN-1-OLYield 86.5%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6342AcetonitrileSolvent

Procedure

A mixture of 5-bromopyrimidine (3.96 g), 5-hexynol (2.44 g), dicyclohexylamine (4 g) and acetonitrile (50 ml) was de-oxygenated by bubbline nitrogen through the solution for 10 min. BTPC (150 mg) and copper (I) iodide (25 mg) were added and the mixture was heated to 60°-70° under nitrogen for 1 h, cooled and evaporated in vacuo. Ether (175 ml) was added, the mixture filtered and evaporated in vacuo and the residue purified by FCC. Elution with ether followed by System C (19:1-92:8) gave the title compound as a pale yellow oil (3.79 g), t.l.c. (System C 17:3) Rf 0.55.

Workup

  1. temperaturethe mixture was heated to 60°-70° under nitrogen for 1 h
  2. temperaturecooled
  3. customevaporated in vacuo
  4. additionEther (175 ml) was added
  5. filtrationthe mixture filtered
  6. customevaporated in vacuo
  7. customthe residue purified by FCC
  8. washElution with ether

Sources & evidence

ORD record
ord-927f729192e8411fb3c440a2fd8b46e0
Source dataset
uspto-grants-1991_02
Patent number
US04996218

Reaction notes

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