Ethyl Acetate → (2-Chloropyrimidin-4-yl)quinolin-3-ylamine

HRID 495448Notes

Reaction equation

HRID 495448 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[NH2:9][C:10]1[CH:11]=[N:12][C:13]2[C:18]([CH:19]=1)=[CH:17][CH:16]=[CH:15][CH:14]=2.CCN(C(C)C)C(C)C.CCOC(C)=O>CC(O)C>[Cl:1][C:2]1[N:7]=[C:6]([NH:9][C:10]2[CH:11]=[N:12][C:13]3[C:18]([CH:19]=2)=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 113753-AminoquinolineHCID 775312,4-DichloropyrimidineHCID 81531Diisopropylethylamine

Product 1

HCID 22326846(2-Chloropyrimidin-4-yl)quinolin-3-ylamine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 2,4-dichloropyrimidine (1.0 g, 6.7 mmol), 3-aminoquinoline (1.1 g, 7.79 mmol) and DIEA (2.0 mL, 11.5 mmol) in IPA (8 mL) was heated to reflux for 48 h. The mixture was poured into EtOAc (200 mL) and washed with H2O (100 mL). The organics were dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude was purified via medium pressure liquid chromatography using 50:50 EtOAc/hexanes followed by 100% EtOAc followed by 5:95 MeOH/CH2Cl2 followed by 1.0:10:90 conc. NH4OH/MeOH/CH2Cl2 as the solvent system. (2-Chloropyrimidin-4-yl)-quinolin-3-yl-amine was obtained as a tan solid.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 48 h
  3. washwashed with H2O (100 mL)
  4. dry with materialThe organics were dried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe crude was purified via medium pressure liquid chromatography

Sources & evidence

ORD record
ord-dcd88f54e0b249edb201d535306f0c55
Source dataset
uspto-grants-2005_09
Patent number
US06939874B2

Reaction notes

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