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

HRID 334155노트

반응식

HRID 334155 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
120 °C

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-f4c4b18172de40a689c57303d1527bd7
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08883799B2

반응 노트

불러오는 중…