3,5-Dimethylaniline → (3,5-Dimethylphenyl)-[4-(2,3,4-trimethoxyphenyl)-pyrimid-2-yl]-amine

HRID 497027노트

반응식

HRID 497027 반응식
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([O:16][CH3:17])[C:9]=2[O:18][CH3:19])[CH:5]=[CH:4][N:3]=1.[CH3:20][C:21]1[CH:22]=[C:23]([CH:25]=[C:26]([CH3:28])[CH:27]=1)[NH2:24].[H-].[Na+].O1CCCC1>C(OCC)C>[CH3:20][C:21]1[CH:22]=[C:23]([NH:24][C:2]2[N:7]=[C:6]([C:8]3[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([O:16][CH3:17])[C:9]=3[O:18][CH3:19])[CH:5]=[CH:4][N:3]=2)[CH:25]=[C:26]([CH3:28])[CH:27]=1

참가 물질

6

반응물 4

HCID 79493,5-DimethylanilineHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 223181282-Chloro-4-(2,3,4-trimethoxyphenyl)pyrimidine

생성물 1

HCID 22318125(3,5-Dimethylphenyl)-[4-(2,3,4-trimethoxyphenyl)-pyrimid-2-yl]-amine

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

In a vial was placed 28 mg (100 μmol) of chloropyrimidine 5, 3,5 dimethylaniline (24 mg, 200 μmol), 60% NaH (6 mg, excess), and tetrakis(triphenylphospine)palladium (6 mg, catalytic). Tetrahydrofuran (2 mL) was added and the vial was sealed and heated to reflux for two hours. The reaction was diluted with diethyl ether and washed with 1N hydrochloric acid. The organic layer was separated, washed with 1N NaOH solution, water, and brine. The organic extract was dried (MgSO4), filtered, and evaporated in vacuo to afford the crude product. The compound was purified on silica gel using an eluent of 20% acetone/hexane to afford the pure product II-14 as a white solid. 1H-NMR (CDCl3, 500 MHz) δ 8.41 (d, 1H), 7.78 (d, 1H), 7.35 (d, 1H), 7.31 (s, 1H), 7.08 (s, 1H), 6.82 (d, 1H), 6.68 (s, 1H), 3.94 (s, 3H), 3.91 (s, 3H), 3.83 (s, 3H), 2.34 (s, 6H).

후처리

  1. customthe vial was sealed
  2. temperatureheated
  3. temperatureto reflux for two hours
  4. washwashed with 1N hydrochloric acid
  5. customThe organic layer was separated
  6. washwashed with 1N NaOH solution, water, and brine
  7. extractionThe organic extract
  8. dry with materialwas dried (MgSO4)
  9. filtrationfiltered
  10. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-b5985219ae34464f975813fec2ca6f8e
출처 데이터셋
uspto-grants-2005_09
특허 번호
US06949544B2

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