Cesium carbonate → N-tert-Butyl-3-[(2-chloro-5-methylpyrimidin-4-yl)amino]benzene-1-sulfonamide

HRID 1912177Notes

Reaction equation

HRID 1912177 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([CH3:9])=[CH:4][N:3]=1.Br[C:11]1[CH:12]=[C:13]([S:17]([NH:20][C:21]([CH3:24])([CH3:23])[CH3:22])(=[O:19])=[O:18])[CH:14]=[CH:15][CH:16]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C(Cl)Cl.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]>[C:21]([NH:20][S:17]([C:13]1[CH:14]=[CH:15][CH:16]=[C:11]([NH:8][C:6]2[C:5]([CH3:9])=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=2)[CH:12]=1)(=[O:19])=[O:18])([CH3:24])([CH3:22])[CH3:23]

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 43021752-Chloro-5-methylpyrimidin-4-amineHCID 48209263-Bromo-N-tert-butylbenzene-1-sulfonamide

Product 1

HCID 53401091N-tert-Butyl-3-[(2-chloro-5-methylpyrimidin-4-yl)amino]benzene-1-sulfonamideYield 120.8%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-chloro-5-methyl-pyrimidin-4-ylamine (0.4 g, 2.8 mmol), 3-bromo-N-tert-butyl-benzenesulfonamide (1.0 g, 3.4 mmol), Pd2(dba)3 (0.17 g, 0.19 mmol), Xantphos (0.2 g, 3.5 mmol) and cesium carbonate (2.0 g, 6.1 mmol) was suspended in dioxane (25 mL) and heated at reflux under the argon atmosphere for 3 h. The reaction mixture was cooled to room temperature and diluted with DCM (30 mL). The mixture was filtered and the filtrate concentrated in vacuo. The residue was dissolved in EtOAc and hexanes added until solid precipitated. After filtration, the title compound (1.2 g, 98%) was obtained as a light brown solid. It was used in the next step without purification. MS (ES+): m/z 355 (M+H)+.

Workup

  1. temperatureheated
  2. temperatureat reflux under the argon atmosphere for 3 h
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate concentrated in vacuo
  5. dissolutionThe residue was dissolved in EtOAc
  6. additionhexanes added until solid
  7. customprecipitated
  8. filtrationAfter filtration

Sources & evidence

ORD record
ord-d97b34cdbf204d21935cfb982f4dae1f
Source dataset
uspto-grants-2013_12
Patent number
US08604042B2

Reaction notes

Loading…