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

HRID 404828Notes

Reaction equation

HRID 404828 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].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 11430Potassium CarbonateHCID 57708264N2-(6-chloropyrimidin-4-yl)pyridine-2,6-diamine

Product 1

HCID 57708273N4-(6-aminopyridin-2-yl)-N6-phenylpyrimidine-4,6-diamineYield 37.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a stirring solution of 2 (0.25 g, 1.235 mmol) and K2CO3 (0.512 g, 3.705 mmol) in dry DMF (2.5 mL) was added 1 (0.320 g, 1.235 mmol) at rt, and the reaction was stirred at 110° C. for 16 h under nitrogen atmosphere. The reaction mixture was quenched with water and extracted with ethyl acetate (3×5 mL). The combined extracts were washed with water (2×25 mL), brine (25 mL), dried over Na2SO4 and concentrated under reduced pressure to give 3 (0.130 g, 21%) as a white solid, which was used in the next step without purification.

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with ethyl acetate (3×5 mL)
  3. washThe combined extracts were washed with water (2×25 mL), brine (25 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8df562bf79254bd3b067ae7912967056
Source dataset
uspto-grants-2014_06
Patent number
US08748606B2

Reaction notes

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