Water → N4-Quinolin-3-yl-N2-(3,4,5-trimethoxyphenyl)pyrimidine-2,4-diamine

HRID 495451Notes

Reaction equation

HRID 495451 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:10]=[N:11][C:12]3[C:17]([CH:18]=2)=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:5]=[CH:4][N:3]=1.[CH3:19][O:20][C:21]1[CH:22]=[C:23]([CH:25]=[C:26]([O:30][CH3:31])[C:27]=1[O:28][CH3:29])[NH2:24].O.C([O-])(O)=O.[Na+]>CC(C)=O.Cl.CCOC(C)=O>[N:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:18]=[C:9]([NH:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH:24][C:23]3[CH:25]=[C:26]([O:30][CH3:31])[C:27]([O:28][CH3:29])=[C:21]([O:20][CH3:19])[CH:22]=3)[N:7]=2)[CH:10]=1

Participants

8

Reactant 4

HCID 962WaterHCID 322853,4,5-TrimethoxyanilineHCID 516892Sodium BicarbonateHCID 22326846(2-Chloropyrimidin-4-yl)quinolin-3-ylamine

Product 1

HCID 10179293N4-Quinolin-3-yl-N2-(3,4,5-trimethoxyphenyl)pyrimidine-2,4-diamine

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (2-chloro-pyrimidin-4-yl)-quinolin-3-yl-amine (100 mg, 0.39 mmol) and 3,4,5-trimethoxyaniline was suspended in acetone (7 mL) and water (2 mL) with 2 drops of conc. HCl. The mixture was heated in a sealed tube to reflux overnight. The mixture was poured into EtOAc (100 mL) and sat. aq. NaHCO3. The organics were separated, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude was purified via preparative HPLC. MS m/z=404. Calc'd for C22H21N5O3: 403.16.

Workup

  1. temperatureThe mixture was heated in a sealed tube
  2. temperatureto reflux overnight
  3. customThe organics were separated
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe crude was purified via preparative HPLC

Sources & evidence

ORD record
ord-5283f8ad221f460b8724247eeece4653
Source dataset
uspto-grants-2005_09
Patent number
US06939874B2

Reaction notes

Loading…