Sodium Bicarbonate → (6-Bromo-pyridin-2-yl)-(2,4-dichloro-pyrimidin-5-yl)-methanone

HRID 1809697노트

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HRID 1809697 반응식
[Br:1][C:2]1[N:7]=[C:6]([CH:8]([C:10]2[C:11]([Cl:17])=[N:12][C:13]([Cl:16])=[N:14][CH:15]=2)[OH:9])[CH:5]=[CH:4][CH:3]=1.C([O-])(O)=O.[Na+].CC1(C)N([O])C(C)(C)CCC1.[O-]Cl.[Na+]>ClCCl.O.CCCC[N+](CCCC)(CCCC)CCCC.[Br-]>[Br:1][C:2]1[N:7]=[C:6]([C:8]([C:10]2[C:11]([Cl:17])=[N:12][C:13]([Cl:16])=[N:14][CH:15]=2)=[O:9])[CH:5]=[CH:4][CH:3]=1

참가 물질

8

반응물 4

HCID 516892Sodium BicarbonateHCID 2724126TempoHCID 23665760Sodium HypochloriteHCID 86667957(6-Bromo-pyridin-2-yl)-(2,4-dichloro-pyrimidin-5-yl)-methanol

생성물 1

HCID 86667958(6-Bromo-pyridin-2-yl)-(2,4-dichloro-pyrimidin-5-yl)-methanone

시약·촉매·용매 3

HCID 74236Tetrabutylammonium Bromide촉매HCID 962Water용매2회HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

To a stirred solution of crude (6-bromo-pyridin-2-yl)-(2,4-dichloro-pyrimidin-5-yl)-methanol (from Example 28 supra) (16.1 g, crude) in dichloromethane (200 mL), water (20 mL) was added followed by NaHCO3 (2.1 g, 25 mmol), TBAB (485 mg, 1.5 mmol) and TEMPO (90 mg, 0.5 mmol). The mixture was then cooled to 0° C. and NaClO (70 mL, active chloride >6.0%) was added slowly and the resulting mixture was stirred for 30 minutes. The mixture was poured into water and extracted with dichloromethane. The organic phase was dried over anhydrous MgSO4, filtered and concentrated. The residue was purified by column chromatography (silica gel, eluting with ethyl acetate:petroleum ether, 1:20) to give (6-bromo-pyridin-2-yl)-(2,4-dichloro-pyrimidin-5-yl)-methanone as a white solid. (Yield 12.7 g, 76% over two steps).

후처리

  1. extractionextracted with dichloromethane
  2. dry with materialThe organic phase was dried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (silica gel, eluting with ethyl acetate:petroleum ether, 1:20)

출처 및 근거

ORD 기록
ord-25de5dddf1f9471b9331a7acf7b73c12
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08362023B2

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