2-Chloro-6-methylaniline → HCID 67389359, compound

HRID 913286Notes

Reaction equation

HRID 913286 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[N:13]=[CH:12][N:11]=[C:10]([NH:14][CH:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)[N:9]=2)[CH:5]=[CH:4][N:3]=1.[Cl:21][C:22]1[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[C:23]=1[NH2:24].C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:21][C:22]1[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[C:23]=1[NH:24][C:2]1[N:7]=[C:6]([C:8]2[N:13]=[CH:12][N:11]=[C:10]([NH:14][CH:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)[N:9]=2)[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 68972-Chloro-6-methylanilineHCID 10796Cesium carbonateHCID 86646774HCID 86646774, compound2×

Product 1

HCID 67389359HCID 67389359, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

To a solution of 4-(2-chloro-4-pyrimidinyl)-N-(tetrahydro-2H-pyran-4-yl)-1,3,5-triazin-2-amine (i.e., the product of Step A) (125 mg, 0.42 mmol) in toluene (4.0 mL) under nitrogen was added 2-chloro-6-methylaniline (180 mg, 1.27 mmol), cesium carbonate (273 mg, 0.84 mmol), tris(dibenzylideneacetone)dipalladium(0) (20 mg, 0.022 mmol), and ((±)-BINAP) (28 mg, 0.044 mmol), and the resulting mixture was stirred and heated at reflux for 6 h. After cooling to room temperature, the mixture was concentrated and purified using column chromatography on silica gel eluted with 40% acetone in hexanes to give 57 mg of the title compound as a yellow solid.

Workup

  1. temperatureheated
  2. temperatureat reflux for 6 h
  3. concentrationthe mixture was concentrated
  4. custompurified
  5. washeluted with 40% acetone in hexanes

Sources & evidence

ORD record
ord-48f9f88e931d407cab8fbfc0bb269a36
Source dataset
uspto-grants-2011_09
Patent number
US08026359B2

Reaction notes

Loading…