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

HRID 1956083노트

반응식

HRID 1956083 반응식
[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]

참가 물질

7

반응물 2

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

생성물 1

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

시약·촉매·용매 4

HCID 11776Triphenylphosphine촉매HCID 83717Copper iodide촉매HCID 178418476HCID 178418476, 화합물촉매HCID 8471Triethylamine용매

반응 조건

온도
90 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-0a96ed2e483e48e98e71a1cefb0b1793
출처 데이터셋
uspto-grants-1998_07
특허 번호
US05779934

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