3-Chloroaniline → HCID 86646784, compound

HRID 913302Notes

Reaction equation

HRID 913302 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[C:12]([NH:14][CH:15]([CH3:19])[CH2:16][O:17][CH3:18])[N:11]=[CH:10][N:9]=2)[CH:5]=[CH:4][N:3]=1.[Cl:20][C:21]1[CH:22]=[C:23]([CH:25]=[CH:26][CH:27]=1)[NH2:24].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>O1CCOCC1>[Cl:20][C:21]1[CH:22]=[C:23]([NH:24][C:2]2[N:7]=[C:6]([C:8]3[CH:13]=[C:12]([NH:14][CH:15]([CH3:19])[CH2:16][O:17][CH3:18])[N:11]=[CH:10][N:9]=3)[CH:5]=[CH:4][N:3]=2)[CH:25]=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 79323-ChloroanilineHCID 521998p-Toluenesulfonic acid monohydrateHCID 86646783HCID 86646783, compound2×

Product 1

HCID 86646784HCID 86646784, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2′-chloro-N-(2-methoxy-1-methylethyl) [4,4′-bipyrimidine]-6-amine (i.e., the product of Step C) (100 mg, 0.357 mmol) and 3-chloroaniline (57 mg, 0.45 mmol) in 1,4-dioxane (3.5 mL) under a nitrogen atmosphere was added p-toluenesulfonic acid monohydrate (57 mg, 0.30 mmol). The resulting mixture was stirred at 100° C. for 18 h. The solution was concentrated under reduced pressure to give a yellow solid residue. The residue was then purified on silica gel eluted with 40% ethyl acetate in hexanes, followed by acetone to give 113 mg of title compound as a solid.

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. customto give a yellow solid residue
  3. customThe residue was then purified on silica gel
  4. washeluted with 40% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-af969c1842ff435287ac5d281ff7d17b
Source dataset
uspto-grants-2011_09
Patent number
US08026359B2

Reaction notes

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