Potassium Acetate → Ammonium Hydroxide

HRID 1482878ノート

反応式

HRID 1482878 の反応式
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]

参加物

7

反応物 3

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

生成物 2

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

試薬・触媒・溶媒 2

HCID 2734559Bis(tricyclohexylphosphine) palladium(0)触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
85 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-079a5406fcc840e19262daf8827ce7c0
出典データセット
uspto-grants-2016_08
特許番号
US09416111B2

反応ノート

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