Riboflavin → 4-(3-(tetrahydro-2H-pyran-4-yl)pyrazin-2-yloxy)aniline

HRID 473682

반응식

HRID 473682 반응식
[O:1]1[CH2:6][CH:5]=[C:4]([C:7]2[C:8]([O:13][C:14]3[CH:20]=[CH:19][C:17]([NH2:18])=[CH:16][CH:15]=3)=[N:9][CH:10]=[CH:11][N:12]=2)[CH2:3][CH2:2]1.CC1C=C2N=C3C(=NC(NC3=O)=O)N(C[C@H](O)[C@H](O)[C@H](O)CO)C2=CC=1C>C(O)C.[OH-].[Pd+2].[OH-].[Pd]>[O:1]1[CH2:2][CH2:3][CH:4]([C:7]2[C:8]([O:13][C:14]3[CH:20]=[CH:19][C:17]([NH2:18])=[CH:16][CH:15]=3)=[N:9][CH:10]=[CH:11][N:12]=2)[CH2:5][CH2:6]1

참가 물질

6

반응물 2

HCID 493570RiboflavinHCID 593739514-(3-(3,6-dihydro-2H-pyran-4-yl)pyrazin-2-yloxy)aniline

생성물 1

HCID 593511704-(3-(tetrahydro-2H-pyran-4-yl)pyrazin-2-yloxy)aniline수율 59.7%

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 9942167Palladium hydroxide촉매HCID 702Ethanol용매

실험 절차

A solution of 4-(3-(3,6-dihydro-2H-pyran-4-yl)pyrazin-2-yloxy)aniline (1.09 g, 4.0 mmol) in ethanol (40 mL) was added palladium hydroxide, 20 wt. % Pd (dry basis) on carbon, wet, Degussa type E101 NEW (0.284 g, 0.405 mmol) and hydrogenated (double-walled balloon pressure) at room temperature for 4 h. The reaction mixture was filtered via a pad of Celite, and the filtrate was concentrated in vacuo and chromatographed via flash column chromatography (20% to 80% EtOAc/Hexanes) to give 4-(3-(tetrahydro-2H-pyran-4-yl)pyrazin-2-yloxy)aniline (0.648 g, 59% yield) as a white solid. [M+1]=272.0.

후처리

  1. filtrationThe reaction mixture was filtered via a pad of Celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. customchromatographed via flash column chromatography (20% to 80% EtOAc/Hexanes)

출처 및 근거

ORD 기록
ord-00ee64f917f74caa86f80c1ca336e211
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637500B2

연결된 노트

불러오는 중…