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

HRID 1809697ノート

反応式

HRID 1809697 の反応式
[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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 74236Tetrabutylammonium Bromide触媒HCID 962Water溶媒2 回HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-25de5dddf1f9471b9331a7acf7b73c12
出典データセット
uspto-grants-2013_01
特許番号
US08362023B2

反応ノート

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