Potassium Fluoride → 3-(benzyloxy)-1-methyl-5-(4-phenylpyrimidin-2-yl)pyridin-2(1H)-one

HRID 625953

반응식

HRID 625953 반응식
[CH2:1]([O:8][C:9]1[C:14](=[O:15])[N:13]([CH3:16])[CH:12]=[C:11](B(O)O)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:21]1[N:26]=[C:25]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:24]=[CH:23][N:22]=1.[F-].[K+]>O1CCOCC1.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[CH2:1]([O:8][C:9]1[C:14](=[O:15])[N:13]([CH3:16])[CH:12]=[C:11]([C:21]2[N:26]=[C:25]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH:24]=[CH:23][N:22]=2)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

6

반응물 3

HCID 522689Potassium FluorideHCID 6053562-Chloro-4-phenylpyrimidineHCID 67404944[5-(Benzyloxy)-1-methyl-6-oxo-1,6-dihydropyridin-3-yl]boronic acid

생성물 1

HCID 674194493-(benzyloxy)-1-methyl-5-(4-phenylpyrimidin-2-yl)pyridin-2(1H)-one수율 49%

시약·촉매·용매 2

HCID 178418851HCID 178418851, 화합물촉매HCID 312751,4-Dioxane용매

반응 조건

온도
60 °C

실험 절차

A mixture of [5-(benzyloxy)-1-methyl-6-oxo-1,6-dihydropyridin-3-yl]boronic acid (30 mg, 0.116 mmol), 2-chloro-4-phenylpyrimidine (23.2 mg, 0.122 mmol), bis(tri-t-butylphosphine)palladium(0) (5.9 mg, 0.012 mmol) and potassium fluoride (24 mg, 0.405 mmol) in dioxane (1.5 mL) was stirred at 60° C. for 22 h, cooled to room temperature and filtered through a plug of silica gel (washed with EtOAc). Combined filtrate and washings were concentrated. Purification by preparative HPLC (5-55% CH3CN/H2O over 20 min, 0.05% added TFA) afforded 21 mg 3-(benzyloxy)-1-methyl-5-(4-phenylpyrimidin-2-yl)pyridin-2(1H)-one (49%) as a yellow solid. LC/MS (M+H)+ 370.3.

후처리

  1. temperaturecooled to room temperature
  2. filtrationfiltered through a plug of silica gel (washed with EtOAc)
  3. concentrationCombined filtrate and washings were concentrated
  4. customPurification
  5. additionby preparative HPLC (5-55% CH3CN/H2O over 20 min, 0.05% added TFA)

출처 및 근거

ORD 기록
ord-3aae46562f2d492eb39237faeaf24c99
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309199B2

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