1,4-Dioxane → 2-(4-morpholinyl)-5-Pyrimidinol

HRID 1021216

반응식

HRID 1021216 반응식
Br[C:2]1[CH:3]=[N:4][C:5]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[N:6][CH:7]=1.CC1(C)C(C)(C)OB(B2OC(C)(C)C(C)(C)O2)[O:16]1.C([O-])(=O)C.[K+].O1CCOCC1>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CCOC(C)=O.O>[N:8]1([C:5]2[N:4]=[CH:3][C:2]([OH:16])=[CH:7][N:6]=2)[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1

참가 물질

8

반응물 4

HCID 312751,4-DioxaneHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 51443624-(5-Bromopyrimidin-2-yl)morpholine

생성물 1

HCID 198710352-(4-morpholinyl)-5-Pyrimidinol수율 41.1%

시약·촉매·용매 3

HCID 178418476HCID 178418476, 화합물촉매HCID 962Water용매HCID 8857Ethyl Acetate용매

반응 조건

온도
80 °C

실험 절차

A mixture of 4-(5-bromopyrimidin-2-yl)morpholine (2 g), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi-1,3,2-dioxaborolane (2.5 g), bis(triphenylphosphine)palladium chloride (180 mg), potassium acetate (2.5 g), and dioxane (20 ml) was stirred at 80° C. overnight under argon atmosphere. Water and EtOAc were added to the reaction mixture, and the organic layer was dried over MgSO4 and concentrated under reduced pressure. The obtained residue was mixed with THF (10 ml) and water (10 ml), and sodium perborate.tetrahydrate (3.5 g) was added thereto, followed by stirring at room temperature overnight. Then, a saturated aqueous ammonium chloride solution was added thereto. The aqueous layer was extracted with EtOAc, and the organic layer was dried over MgSO4 and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/EtOAc) to obtain 2-(morpholin-4-yl)pyrimidin-5-ol (610 mg).

후처리

  1. dry with materialthe organic layer was dried over MgSO4
  2. concentrationconcentrated under reduced pressure
  3. additionThe obtained residue was mixed with THF (10 ml) and water (10 ml), and sodium perborate
  4. additiontetrahydrate (3.5 g) was added
  5. stirringby stirring at room temperature overnight
  6. additionThen, a saturated aqueous ammonium chloride solution was added
  7. extractionThe aqueous layer was extracted with EtOAc
  8. dry with materialthe organic layer was dried over MgSO4
  9. concentrationconcentrated under reduced pressure
  10. customThe obtained residue was purified by silica gel column chromatography (hexane/EtOAc)

출처 및 근거

ORD 기록
ord-0113e6ff68014374a71b35e65f9ae46c
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08716470B2

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