2,4-Hexadienal → 4-ethoxy-7-(4-[{2E,4E}-1-hydroxyhexa-2,4-dienyl]phenyl)-9-methyl-2-piperazin-1-yl-thieno[2,3-d:4,5-d']dipyrimidine

HRID 556402노트

반응식

HRID 556402 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([CH3:30])[C:11]3[C:16]4[N:17]=[C:18]([N:24]5[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]5)[N:19]=[C:20]([O:21][CH2:22][CH3:23])[C:15]=4[S:14][C:12]=3[N:13]=2)=[CH:4][CH:3]=1.[Li]CCCC.[CH:36](=[O:42])/[CH:37]=[CH:38]/[CH:39]=[CH:40]/[CH3:41]>C1COCC1>[CH2:22]([O:21][C:20]1[C:15]2[S:14][C:12]3[N:13]=[C:8]([C:5]4[CH:6]=[CH:7][C:2]([CH:36]([OH:42])/[CH:37]=[CH:38]/[CH:39]=[CH:40]/[CH3:41])=[CH:3][CH:4]=4)[N:9]=[C:10]([CH3:30])[C:11]=3[C:16]=2[N:17]=[C:18]([N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)[N:19]=1)[CH3:23]

참가 물질

5

반응물 3

HCID 6375642,4-HexadienalHCID 597550637-(4-Bromophenyl)-4-ethoxy-9-methyl-2-piperazin-1-yl-thieno[2,3-d:4,5-d']dipyrimidineHCID 178418339Butyllithium

생성물 1

HCID 597551404-ethoxy-7-(4-[{2E,4E}-1-hydroxyhexa-2,4-dienyl]phenyl)-9-methyl-2-piperazin-1-yl-thieno[2,3-d:4,5-d']dipyrimidine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-10 °C

실험 절차

200 mg (0.4 mmol) 7-(4-bromophenyl)-4-ethoxy-9-methyl-2-piperazin-1-yl-thieno[2,3-d:4,5-d′]dipyrimidine was mixed at −80° C. in 50 ml THF with 0.48 ml (1.2 mmol) 2.5 M BuLi solution. After 15 min at this temperature, 112 mg (1.2 mmol) (2E,4E) hexadienal was added. Subsequently, the reaction mixture was heated to −10° C. and the reaction was terminated by addition of 10 ml saturated NaHCO3. The organic solvent was removed and the aqueous phase was extracted with CH2Cl2. Following flash chromatographic purification (CH2Cl2/methanol, 8:2) 130 mg (63%) of the title compound was obtained. ESI-MS [m/z]: 503, melting point: 149-150° C.

후처리

  1. customthe reaction was terminated by addition of 10 ml saturated NaHCO3
  2. customThe organic solvent was removed
  3. extractionthe aqueous phase was extracted with CH2Cl2
  4. customchromatographic purification (CH2Cl2/methanol, 8:2) 130 mg (63%) of the title compound
  5. customwas obtained

출처 및 근거

ORD 기록
ord-77ed455c0b5948c18958643106953be5
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08058285B2

반응 노트

불러오는 중…