Diisobutylaluminum hydride → 1-(2,4-Dichloro-6-morpholin-4-yl-pyrimidin-5-yloxy)-propan-2-ol

HRID 528459노트

반응식

HRID 528459 반응식
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([O:9][CH2:10][C:11](=[O:13])[CH3:12])=[C:4]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[N:3]=1.CC(C[AlH]CC(C)C)C>C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([O:9][CH2:10][CH:11]([OH:13])[CH3:12])=[C:4]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[N:3]=1

참가 물질

4

반응물 2

HCID 14487Diisobutylaluminum hydride2회HCID 867117441-(2,4-Dichloro-6-morpholin-4-yl-pyrimidin-5-yloxy)-propan-2-one

생성물 1

HCID 867117451-(2,4-Dichloro-6-morpholin-4-yl-pyrimidin-5-yloxy)-propan-2-ol수율 100.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

To a solution of 1-(2,4-dichloro-6-morpholin-4-yl-pyrimidin-5-yloxy)-propan-2-one (146 mg, 0.48 mmol) in THF (5 mL) at −78° C. was added DIBAL-H (580 μL, 0.58 mmol, 1M solution in toluene) and the resulting mixture warmed to 0° C. and stirred for 1.5 hours. The reaction mixture was cooled to −78° C. before the addition of further DIBAL-H (480 μL, 0.48 mmol) and the mixture warmed to 0° C. and stirred for 2 hours. The reaction mixture was quenched with Rochelle's salt (1M aqueous solution) and the mixture extracted with ethyl acetate. The combined organic extracts were washed with brine, then dried (Na2SO4) and concentrated in vacuo affording 1-(2,4-Dichloro-6-morpholin-4-yl-pyrimidin-5-yloxy)-propan-2-ol (148 mg, quantitative). LCMS: RT=2.84 min, [M+H]+=308/310/312.

후처리

  1. temperaturethe mixture warmed to 0° C.
  2. stirringstirred for 2 hours
  3. customThe reaction mixture was quenched with Rochelle's salt (1M aqueous solution)
  4. extractionthe mixture extracted with ethyl acetate
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-d8d987ebbeb84be0b0541911afcb33df
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346817B2

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