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

HRID 404827Notes

Reaction equation

HRID 404827 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]([NH2:15])[N:10]=2)[CH:3]=1.C([O-])([O-])=O.[K+].[K+].[NH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C=O)C>[NH2:15][C:11]1[N:10]=[C:9]([NH:8][C:4]2[CH:3]=[C:2]([NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[N:7]=[CH:6][N:5]=2)[CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 11430Potassium CarbonateHCID 57708264N2-(6-chloropyrimidin-4-yl)pyridine-2,6-diamine

Product 1

HCID 57708273N4-(6-aminopyridin-2-yl)-N6-phenylpyrimidine-4,6-diamineYield 64.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring solution of 1 (2.0 g, 10.75 mmol) and K2CO3 (2.96 g, 21.5 mmol) in dry DMF (20 mL) was added 2 (1.59 g, 10.75 mmol) and the reaction mixture was stirred at rt for 16 h under nitrogen atmosphere. It was cooled, quenched with water (100 mL) and extracted with EtOAc (2×50 mL). The combined EtOAc extract was washed with 10% NaHCO3 soln. (50 mL), water (3×50 mL), brine (50 mL), dried over Na2SO4 and concentrated under reduced pressure to give 3 (1.92 g, 60.0%) as a light yellow solid, which was used in the next step without further purifications.

Workup

  1. temperatureIt was cooled
  2. customquenched with water (100 mL)
  3. extractionextracted with EtOAc (2×50 mL)
  4. extractionThe combined EtOAc extract
  5. washwas washed with 10% NaHCO3 soln
  6. dry with material(50 mL), water (3×50 mL), brine (50 mL), dried over Na2SO4
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c1d3b4a02a7b4c74805064ea2efe7b73
Source dataset
uspto-grants-2014_06
Patent number
US08748606B2

Reaction notes

Loading…