Imidazole → HCID 58507769、化合物

HRID 253021ノート

反応式

HRID 253021 の反応式
[N:1]1([C:7]2[C:8]3[S:22][CH:21]=[CH:20][C:9]=3[N:10]=[C:11]([C:13]3[CH:14]=[C:15]([OH:19])[CH:16]=[CH:17][CH:18]=3)[N:12]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.N1C=CN=C1.[Si:28](Cl)([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29]>CN(C=O)C>[C:31]([Si:28]([CH3:30])([CH3:29])[O:19][C:15]1[CH:14]=[C:13]([C:11]2[N:12]=[C:7]([N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]3)[C:8]3[S:22][CH:21]=[CH:20][C:9]=3[N:10]=2)[CH:18]=[CH:17][CH:16]=1)([CH3:34])([CH3:33])[CH3:32]

参加物

5

反応物 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 99013723-(4-Morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl)phenol

生成物 1

HCID 58507769HCID 58507769、化合物収率 83.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

A mixture of 3-(4-morpholin-4-yl-thieno[3,2-d]pyrimidin-2-yl)-phenol (17.28 g, 55.1 mmol), imidazole (1.7 eq., 93.7 mmol, 6.38 g) and tert-butyldimethylsilyl chloride (1.5 eq., 82.7 mmol. 12.47 g) in DMF (45 mL) was heated at 50° C. for 5 hours. The reaction mixture was then cooled and partitioned between water (400 mL) and ether (3×400 mL). The combined organic layers were washed sequentially with saturated aqueous sodium hydrogen carbonate (300 mL), brine (300 mL), separated and dried (MgSO4). The crude product was evaporated onto silica and purified by chromatography (5%→20% ethyl acetate-petrol) to yield compound 7 as a white solid (19.60 g, 83%).

後処理

  1. temperatureThe reaction mixture was then cooled
  2. custompartitioned between water (400 mL) and ether (3×400 mL)
  3. washThe combined organic layers were washed sequentially with saturated aqueous sodium hydrogen carbonate (300 mL), brine (300 mL)
  4. customseparated
  5. dry with materialdried (MgSO4)
  6. customThe crude product was evaporated onto silica
  7. custompurified by chromatography (5%→20% ethyl acetate-petrol)

出典と根拠

ORDレコード
ord-b917dea8f2c34f5abb91add11e1aa07a
出典データセット
uspto-grants-2011_01
特許番号
US07872003B2

反応ノート

読み込み中…