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 556402ノート

反応式

HRID 556402 の反応式
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]

参加物

5

反応物 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

生成物 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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-10 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-77ed455c0b5948c18958643106953be5
出典データセット
uspto-grants-2011_11
特許番号
US08058285B2

反応ノート

読み込み中…