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

HRID 982376ノート

反応式

HRID 982376 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>[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

参加物

6

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 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒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 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.

後処理

  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

出典と根拠

ORDレコード
ord-927f729192e8411fb3c440a2fd8b46e0
出典データセット
uspto-grants-1991_02
特許番号
US04996218

反応ノート

読み込み中…