Stannous chloride dihydrate → 2,4-Dimethyl-3-(3-(pyrimidin-4-yl)pyridin-2-yloxy)benzenamine

HRID 1361687노트

반응식

HRID 1361687 반응식
O.O.[Sn](Cl)Cl.[CH3:6][C:7]1[C:25]([N+:26]([O-])=O)=[CH:24][CH:23]=[C:22]([CH3:29])[C:8]=1[O:9][C:10]1[C:15]([C:16]2[CH:21]=[CH:20][N:19]=[CH:18][N:17]=2)=[CH:14][CH:13]=[CH:12][N:11]=1>CO>[CH3:6][C:7]1[C:8]([O:9][C:10]2[C:15]([C:16]3[CH:21]=[CH:20][N:19]=[CH:18][N:17]=3)=[CH:14][CH:13]=[CH:12][N:11]=2)=[C:22]([CH3:29])[CH:23]=[CH:24][C:25]=1[NH2:26]

참가 물질

4

반응물 2

HCID 61436Stannous chloride dihydrateHCID 669706854-(2-(2,6-Dimethyl-3-nitrophenoxy)pyridin-3-yl)pyrimidine

생성물 1

HCID 669703062,4-Dimethyl-3-(3-(pyrimidin-4-yl)pyridin-2-yloxy)benzenamine

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

Added tin(II) chloride dihydrate (6.13 g, 27.1 mmol) to a stirring solution/suspension of 4-(2-(2,6-dimethyl-3-nitrophenoxy)pyridin-3-yl)pyrimidine (1.75 g, 5.43 mmol) in methanol (20.0 ml). Heated reaction mixture to 65° C. for 1.25 hours. Filtered hot suspension through Celite which was washed with 20 mL MeOH and 200 mL EtOAc. The organic solution was then extracted with 3×100 1N HCl. The acidic aqueous phase was then basified with 5N NaOH and allowed to stand for 5 minutes. The aqueous phase was then extracted with 3×150 mL portions of CHCl3 which was collected as a bright red-orange solution, dried over sodium sulfate and concentrated in vacuo to afford a brown solid. This was purified by column chromatography (10-100% (2.0 M NH3 in MeOH) in dichloromethane) and concentrated to afford 2,4-dimethyl-3-(3-(pyrimidin-4-yl)pyridin-2-yloxy)benzenamine as a bright red-orange solid. MS m/z=293 (M+H)+. Calc'd for C17H16N4O: 292.34.

후처리

  1. temperatureHeated
  2. customreaction mixture to 65° C. for 1.25 hours
  3. filtrationFiltered hot suspension through Celite which
  4. washwas washed with 20 mL MeOH and 200 mL EtOAc
  5. extractionThe organic solution was then extracted with 3×100 1N HCl
  6. extractionThe aqueous phase was then extracted with 3×150 mL portions of CHCl3 which
  7. customwas collected as a bright red-orange solution
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated in vacuo
  10. customto afford a brown solid
  11. customThis was purified by column chromatography (10-100% (2.0 M NH3 in MeOH) in dichloromethane)
  12. concentrationconcentrated

출처 및 근거

ORD 기록
ord-c9a6ca3bf3d6443d8478d3412fa2443e
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07880000B2

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