(4-Aminophenoxy)benzene → N4-(6-(methylamino)pyridine-2-yl)-N6-(4-phenoxyphenyl)pyrimidine-4,6-diamine

HRID 1053212Notes

Reaction equation

HRID 1053212 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([NH:15][CH3:16])[N:10]=2)[CH:3]=1.[O:17]([C:24]1[CH:30]=[CH:29][C:27]([NH2:28])=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>Cl.C(O)CCC>[CH3:16][NH:15][C:11]1[N:10]=[C:9]([NH:8][C:4]2[CH:3]=[C:2]([NH:28][C:27]3[CH:26]=[CH:25][C:24]([O:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:30][CH:29]=3)[N:7]=[CH:6][N:5]=2)[CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 8764(4-Aminophenoxy)benzeneHCID 57708344n2-(6-Chloropyrimidin-4-yl)-n6-methylpyridine-2,6,diamine

Product 1

HCID 57708271N4-(6-(methylamino)pyridine-2-yl)-N6-(4-phenoxyphenyl)pyrimidine-4,6-diamineYield 41%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 2631-ButanolSolvent

Procedure

A solution of N2-(6-chloropyrimidin-4-yl)-N6-methylpyridine-2,6,diamine (0.3 g 1.27 mmol), 4-phenoxy aniline (0.28 g, 1.52 mmol) and conc. HCl (2 drops) in n-butanol (2 mL) was subjected to microwave irradiation (120° C., 1 h). The reaction mixture was cooled, was concentrated under reduced pressure, and the residue was diluted with CH2Cl2 (5 mL). The dichloromethane solution was washed with NaHCO3 (2 mL), water (2 mL), and brine (2 mL), and was dried over Na2SO4. Filtration followed by concentration under reduced pressure gave a residue which was purified by column chromatography (SiO2, 60-120, chloroform/methanol, 9/1) to give N4-(6-(methylamino)pyridine-2-yl)-N6-(4-phenoxyphenyl)pyrimidine-4,6-diamine (0.2 g, 41%) as a light brown solid.

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationwas concentrated under reduced pressure
  3. additionthe residue was diluted with CH2Cl2 (5 mL)
  4. washThe dichloromethane solution was washed with NaHCO3 (2 mL), water (2 mL), and brine (2 mL)
  5. dry with materialwas dried over Na2SO4
  6. filtrationFiltration
  7. concentrationfollowed by concentration under reduced pressure
  8. customgave a residue which
  9. customwas purified by column chromatography (SiO2, 60-120, chloroform/methanol, 9/1)

Sources & evidence

ORD record
ord-15919d88007440049e1220051f054f1e
Source dataset
uspto-grants-2016_07
Patent number
US09393246B2

Reaction notes

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