Sodium Carbonate → 6-(4-aminophenyl)-N-[(1S)-1-phenylethyl]pyrazin-2-amine

HRID 1244408노트

반응식

HRID 1244408 반응식
Cl[C:2]1[N:7]=[C:6]([NH:8][C@H:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH3:10])[CH:5]=[N:4][CH:3]=1.CC1(C)C(C)(C)OB([C:25]2[CH:31]=[CH:30][C:28]([NH2:29])=[CH:27][CH:26]=2)O1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:29][C:28]1[CH:30]=[CH:31][C:25]([C:2]2[N:7]=[C:6]([NH:8][C@H:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH3:10])[CH:5]=[N:4][CH:3]=2)=[CH:26][CH:27]=1

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 587170806-Chloro-N-[(1S)-1-phenylethyl]pyrazin-2-amine

생성물 1

HCID 587170936-(4-aminophenyl)-N-[(1S)-1-phenylethyl]pyrazin-2-amine

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 1140Toluene용매

실험 절차

A mixture of 6-chloro-N-[(1S)-1-phenylethyl]pyrazin-2-amine (1.10 g, 4.71 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) aniline (1.10 g, 5.02 mmol), (PPh3)4Pd (580 mg, 0.5 mmol) and a Na2CO3 solution (2.6 ml, 2M solution) in toluene (20 ml) was heated under reflux for 40 h. Upon cooling, the mixture was diluted with water (30 mL) and the product extracted with ethyl acetate (3×40 ml). The organic layers were combined, washed with brine (30 ml), dried (Na2SO4), and the solvent removed in vacuo. The residue was purified by column chromatography, eluting with a hexane-ethyl acetate (2:3) to furnish the desired product from the polar fractions (0.86 g, 63%).

후처리

  1. temperatureunder reflux for 40 h
  2. temperatureUpon cooling
  3. extractionthe product extracted with ethyl acetate (3×40 ml)
  4. washwashed with brine (30 ml)
  5. dry with materialdried (Na2SO4)
  6. customthe solvent removed in vacuo
  7. customThe residue was purified by column chromatography
  8. washeluting with a hexane-ethyl acetate (2:3)

출처 및 근거

ORD 기록
ord-6911be29f3504cf2bdba68e191247300
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07122550B2

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