Potassium Acetate → Ammonium Hydroxide

HRID 1482878노트

반응식

HRID 1482878 반응식
Cl[C:2]1[CH:3]=[N:4][C:5]([CH2:8][CH2:9][C:10]([O-:12])=[O:11])=[N:6][CH:7]=1.[B:13]1(B2OC(C)(C)C(C)(C)O2)[O:17]C(C)(C)C(C)(C)[O:14]1.[C:31]([O-])(=O)[CH3:32].[K+]>O1CCOCC1.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.[Pd]>[OH-:11].[NH4+:4].[CH2:31]([O:12][C:10](=[O:11])[CH2:9][CH2:8][C:5]1[N:4]=[CH:3][C:2]([B:13]([OH:17])[OH:14])=[CH:7][N:6]=1)[CH3:32]

참가 물질

7

반응물 3

HCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 1317367133-(5-Chloropyrimidin-2-yl)propanoate

생성물 2

HCID 14923Ammonium Hydroxide수율 0.1%HCID 123667257[2-(3-Ethoxy-3-oxopropyl)pyrimidin-5-yl]boronic acid

시약·촉매·용매 2

HCID 2734559Bis(tricyclohexylphosphine) palladium(0)촉매HCID 312751,4-Dioxane용매

반응 조건

온도
85 °C

실험 절차

3-(5-Chloropyrimidin-2-yl)propanoate (1.49 g, 6.97 mmol), bis(pinacolato)diboron (1.95 g, 7.67 mmol), and potassium acetate (1.1 g, 11.15 mmol) were suspended in dioxane (34.8 mL). The system was evacuated and then purged with Ar three times before adding bis(tricyclohexylphosphine)palladium(0) (0.12 g, 0.17 mmol). The system was evacuated and then purged with Ar three times before capping and heating the mixture to 85° C. for 16 hours. The reaction was allowed to cool to room temperature, filtered through CELITE, and concentrated in vacuo. The residue was purified by reverse phase column chromatography using a C18 column eluting with 3:97 to 100:0 acetonitrile:water with 0.1% ammonium hydroxide to give [2-(3-ethoxy-3-oxopropyl)pyrimidin-5-yl]boronic acid. MS ESI calcd for C9H14BN2O4 [M+H]+ 225. found 225. 1H NMR (500 MHz, DMSO-d6) δ 8.89 (s, 1H), 8.52 (s, 1H), 4.00 (q, J=7.1 Hz, 2H), 3.12 (t, J=7.0 Hz, 2H), 2.78 (t, J=7.0 Hz, 2H), 1.11 (t, J=7.1 Hz, 3H).

후처리

  1. customThe system was evacuated
  2. custompurged with Ar three times
  3. customThe system was evacuated
  4. custompurged with Ar three times
  5. temperatureto cool to room temperature
  6. filtrationfiltered through CELITE
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by reverse phase column chromatography
  9. washeluting with 3:97 to 100:0 acetonitrile

출처 및 근거

ORD 기록
ord-079a5406fcc840e19262daf8827ce7c0
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09416111B2

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