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

HRID 1886010ノート

反応式

HRID 1886010 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a6dcb8a042614ccfb934c4ee5fed4e2f
出典データセット
uspto-grants-1992_09
特許番号
US05149698

反応ノート

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