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

HRID 497027Notes

Reaction equation

HRID 497027 reaction equation
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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-b5985219ae34464f975813fec2ca6f8e
Source dataset
uspto-grants-2005_09
Patent number
US06949544B2

Reaction notes

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