5-Decyloxy-2-(4-bromophenyl)pyrimidine → (-)-5-Decyloxy-2-[4-(6-hydroxyheptynyl)phenyl]pyrimidine

HRID 1956083ノート

反応式

HRID 1956083 の反応式
[CH2:1]([O:11][C:12]1[CH:13]=[N:14][C:15]([C:18]2[CH:23]=[CH:22][C:21](Br)=[CH:20][CH:19]=2)=[N:16][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[OH:25][CH:26]([CH3:32])[CH2:27][CH2:28][CH2:29][C:30]#[CH:31]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu](I)I.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C>[CH2:1]([O:11][C:12]1[CH:13]=[N:14][C:15]([C:18]2[CH:23]=[CH:22][C:21]([C:31]#[C:30][CH2:29][CH2:28][CH2:27][CH:26]([OH:25])[CH3:32])=[CH:20][CH:19]=2)=[N:16][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

参加物

7

反応物 2

HCID 114747935-Decyloxy-2-(4-bromophenyl)pyrimidineHCID 133371736-Heptyn-2-ol

生成物 1

HCID 19437556(-)-5-Decyloxy-2-[4-(6-hydroxyheptynyl)phenyl]pyrimidine収率 86.7%

試薬・触媒・溶媒 4

HCID 11776Triphenylphosphine触媒HCID 83717Copper iodide触媒HCID 178418476HCID 178418476、化合物触媒HCID 8471Triethylamine溶媒

反応条件

温度
90 °C

実験手順

In a reactor equipped with a stirrer and a thermometer, 5-decyloxy-2-(4-bromophenyl)pyrimidine (25 g), optically active 6-hydroxy-1-heptyne (8.58 g), dichlorobis(triphenylphosphine)palladium (0.1 g), copper iodide (0.1 g), triphenylphosphine (0.52 g) and triethylamine (200 ml) are charged and heated up to 90° C. to carry out a reaction for 10 hours. After evaporating triethylamine off under reduced pressure, toluene and 10% hydrochloric acid are added to the residue for extraction, and the organic layer is washed with water and evaporated under reduced pressure. A resulting residue is purified by silica gel column chromatography (eluent: hexane-ethyl acetate) to obtain (-)-5-decyloxy-2-[4-(6-hydroxyheptynyl)phenyl]-pyrimidine (23.4 g). [α]D20 =-3.3° (c=1.035, CHCl3).

後処理

  1. customIn a reactor equipped with a stirrer
  2. customa reaction for 10 hours
  3. customAfter evaporating triethylamine off under reduced pressure, toluene and 10% hydrochloric acid
  4. additionare added to the residue for extraction
  5. washthe organic layer is washed with water
  6. customevaporated under reduced pressure
  7. customA resulting residue is purified by silica gel column chromatography (eluent: hexane-ethyl acetate)

出典と根拠

ORDレコード
ord-0a96ed2e483e48e98e71a1cefb0b1793
出典データセット
uspto-grants-1998_07
特許番号
US05779934

反応ノート

読み込み中…