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

HRID 497027ノート

反応式

HRID 497027 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-b5985219ae34464f975813fec2ca6f8e
出典データセット
uspto-grants-2005_09
特許番号
US06949544B2

反応ノート

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