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

HRID 528449
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HRID 528449 반응식
C([O:3][C:4](=O)[CH2:5][O:6][C:7]1[C:8]([Cl:20])=[N:9][C:10]([Cl:19])=[N:11][C:12]=1[N:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1)C.CC(C[AlH]CC(C)C)C>C1COCC1>[Cl:19][C:10]1[N:9]=[C:8]([Cl:20])[C:7]([O:6][CH2:5][CH2:4][OH:3])=[C:12]([N:13]2[CH2:14][CH2:15][O:16][CH2:17][CH2:18]2)[N:11]=1
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HCID 14487Diisobutylaluminum hydrideHCID 86711735(2,4-Dichloro-6-morpholin-4-yl-pyrimidin-5-yloxy)-acetic acid ethyl ester

생성물 1

HCID 867117362-(2,4-Dichloro-6-morpholin-4-yl-pyrimidin-5-yloxy)-ethanol수율 95%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

To a solution of (2,4-dichloro-6-morpholin-4-yl-pyrimidin-5-yloxy)-acetic acid ethyl ester (188 mg, 0.56 mmol) in THF (2.5 mL) at −78° C. was added DIBAL-H (2.0 mL, 2.0 mmol, 1M solution in THF) and the resulting mixture warmed to 0° C. over 30 minutes. The reaction mixture was quenched with methanol and Rochelle's salt (1M aqueous solution) and the aqueous extracted with ethyl acetate. The combined organic extracts were dried (Na2SO4) and concentrated in vacuo affording 2-(2,4-Dichloro-6-morpholin-4-yl-pyrimidin-5-yloxy)-ethanol as an oil (156 mg, 95%). LCMS: RT=2.60 min, [M+H]+=294/296/298.

후처리

  1. customThe reaction mixture was quenched with methanol and Rochelle's salt (1M aqueous solution)
  2. extractionthe aqueous extracted with ethyl acetate
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-923bbcd7db49403fb12e2a09e4ce8b8a
출처 데이터셋
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09346817B2

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