Aniline → N4-(6-aminopyridin-2-yl)-N6-phenylpyrimidine-4,6-diamine

HRID 2193630Notes

Reaction equation

HRID 2193630 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].Cl[C:15]1[N:20]=[CH:19][N:18]=[C:17]([NH:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([NH2:28])[N:23]=2)[CH:16]=1>CN(C=O)C>[NH2:28][C:24]1[N:23]=[C:22]([NH:21][C:17]2[CH:16]=[C:15]([NH:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[N:20]=[CH:19][N:18]=2)[CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 10796Cesium carbonateHCID 57708264N2-(6-chloropyrimidin-4-yl)pyridine-2,6-diamine

Product 1

HCID 57708273N4-(6-aminopyridin-2-yl)-N6-phenylpyrimidine-4,6-diamineYield 36.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 2 (4.35 g, 23.38 mmol) and Cs2CO3 (15.26 g, 46.76 mmol) in dry DMF (50 mL) was added 1 (5.0 g, 15.58 mmol) at rt and the reaction was stirred at 80° C. for 16 h under nitrogen atmosphere. The reaction mixture was cooled, concentrated under reduced pressure and the residue was diluted with ethyl acetate (50 mL). It was washed with water (2×10 mL), brine (10 mL), dried over Na2SO4 and concentrated under reduced pressure. The residue was further purified by column chromatography (SiO2, 60-120, pet ether/ethyl acetate, 5/5) to give 3 (1.6 g, 23.3%) as brown solid.

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated under reduced pressure
  3. additionthe residue was diluted with ethyl acetate (50 mL)
  4. washIt was washed with water (2×10 mL), brine (10 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was further purified by column chromatography (SiO2, 60-120, pet ether/ethyl acetate, 5/5)

Sources & evidence

ORD record
ord-b1199f50b07a4a0f81c08ebcc02198ee
Source dataset
uspto-grants-2012_12
Patent number
US08329901B2

Reaction notes

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