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

HRID 1886010Notes

Reaction equation

HRID 1886010 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>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

5

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 1

HCID 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 bubbling 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. customby bubbling nitrogen through the solution for 10 min
  2. additionBTPC (150 mg) and copper (I) iodide (25 mg) were added
  3. temperaturethe mixture was heated to 60°-70° under nitrogen for 1 h
  4. temperaturecooled
  5. customevaporated in vacuo
  6. additionEther (175 ml) was added
  7. filtrationthe mixture filtered
  8. customevaporated in vacuo
  9. customthe residue purified by FCC
  10. washElution with ether

Sources & evidence

ORD record
ord-a6dcb8a042614ccfb934c4ee5fed4e2f
Source dataset
uspto-grants-1992_09
Patent number
US05149698

Reaction notes

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