Toluene → 3-Chloro-8,8-dimethyl-1-morpholin-4-yl-5,8-dihydro-6H-7-oxa-9-thia-2,4-diaza-fluorene

HRID 334155ノート

反応式

HRID 334155 の反応式
[Cl:1][C:2]1[N:3]=[C:4]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[C:5]2[S:10][C:9]([C:11](O)([CH3:13])[CH3:12])=[C:8]([CH2:15][CH2:16][OH:17])[C:6]=2[N:7]=1.C1(C)C=CC=CC=1.FC(F)(F)C(O)=O>O>[Cl:1][C:2]1[N:3]=[C:4]([N:18]2[CH2:19][CH2:20][O:21][CH2:22][CH2:23]2)[C:5]2[S:10][C:9]3[C:11]([CH3:12])([CH3:13])[O:17][CH2:16][CH2:15][C:8]=3[C:6]=2[N:7]=1

参加物

5

反応物 3

HCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 706766062-(2-Chloro-7-(2-hydroxyethyl)-4-morpholinothieno[3,2-d]pyrimidin-6-yl)propan-2-ol

生成物 1

HCID 706766073-Chloro-8,8-dimethyl-1-morpholin-4-yl-5,8-dihydro-6H-7-oxa-9-thia-2,4-diaza-fluorene収率 35.1%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
120 °C

実験手順

Impure 2-(2-chloro-7-(2-hydroxyethyl)-4-morpholinothieno[3,2-d]pyrimidin-6-yl)propan-2-ol (30 mg) was dissolved in toluene (5 mL, 50 mmol). Trifluoroacetic acid (0.5 mL, 6 mmol) was added and the reaction mixture was heated at 120° C. for two h. Complete reaction was confirmed by LCMS. Diluted with water and extracted with ethyl acetate, dried over magnesium sulfate, concentrated in vacuo and was purified by silica gel chromatography (0 to 100% ethyl acetate/heptanes) on the CombiFlash® Rf system using an amine column and concentrated in vacuo to give 3-Chloro-8,8-dimethyl-1-morpholin-4-yl-5,8-dihydro-6H-7-oxa-9-thia-2,4-diaza-fluorene (10 mg, 10% yield)

後処理

  1. customComplete reaction
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customwas purified by silica gel chromatography (0 to 100% ethyl acetate/heptanes) on the CombiFlash® Rf system
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-f4c4b18172de40a689c57303d1527bd7
出典データセット
uspto-grants-2014_11
特許番号
US08883799B2

反応ノート

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