p-Fluoronitrobenzene → 1-(4-aminophenyl)pyrimidin-2(1H)-one

HRID 642979

반응식

HRID 642979 반응식
Cl.[OH:2][C:3]1[N:8]=[CH:7][CH:6]=[CH:5][N:4]=1.[H-].[Na+].F[C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=1.[Cl-].[NH4+].[In]>CN1C(=O)CCC1.C(O)C.O>[NH2:18][C:15]1[CH:16]=[CH:17][C:12]([N:4]2[CH:5]=[CH:6][CH:7]=[N:8][C:3]2=[O:2])=[CH:13][CH:14]=1

참가 물질

9

반응물 5

HCID 9590p-FluoronitrobenzeneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 5359967IndiumHCID 178479648HCID 178479648, 화합물

생성물 1

HCID 592600731-(4-aminophenyl)pyrimidin-2(1H)-one

시약·촉매·용매 3

HCID 702Ethanol용매HCID 962Water용매HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

2-Hydroxypyrimidine hydrogenchloride (2.1, 1.50 g, 11.3 mmol) was stirred in 20 mL dry NMP at RT. To it was added sodium hydride (60% in mineral oil, 0.95 g, 23.5 mmol) in small portions carefully. The mixture was stirred for 30 min before 4-fluoro-1-nitrobenzene (1.0 mL, 9.4 mmol) was added. The mixture was sent to 80° C. bath and stirred overnight. It was concentrated in vacuo and taken into acetonitrile. After vigorously stirring, the insoluble solid was collected, which was a mixture of leftover 2-hydroxypyrimidine and 1-(4-nitrophenyl)pyrimidin-2(1H)-one 2.2. MS found for C10H7N3O3 (M+H)+ 218.0. This solid (1.27 g, 5.8 mmol) was dissolved in 100 mL ethanol and 30 mL water. To it was added ammonium chloride (3.1 g, 58 mmol) and indium powder (2.6 g, 23 mmol). The mixture was refluxed for 6 hrs. It was concentrated in vacuo, filtered through celite. The solid cake was rinsed with water. The filtrate was concentrated and subjected to reverse phase prep HPLC to isolate 1-(4-aminophenyl)pyrimidin-2(1H)-one 2.3. MS found for C10H9N3O (M+H)+ 188.1.

후처리

  1. additionwas added
  2. customwas sent to 80° C.
  3. concentrationIt was concentrated in vacuo
  4. stirringAfter vigorously stirring
  5. customthe insoluble solid was collected
  6. additiona mixture of leftover 2-hydroxypyrimidine and 1-(4-nitrophenyl)pyrimidin-2(1H)-one 2.2
  7. temperatureThe mixture was refluxed for 6 hrs
  8. concentrationIt was concentrated in vacuo
  9. filtrationfiltered through celite
  10. washThe solid cake was rinsed with water
  11. concentrationThe filtrate was concentrated

출처 및 근거

ORD 기록
ord-2010123e7cce4016a37900a4e870ab35
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07696352B2

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