Cesium carbonate → HCID 57516489, compound

HRID 491203Notes

Reaction equation

HRID 491203 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([CH3:9])=[CH:4][N:3]=1.[C:10]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16](Br)[CH:15]=1)([CH3:13])([CH3:12])[CH3:11].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.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:10]([C:14]1[CH:15]=[C:16]([NH:8][C:6]2[C:5]([CH3:9])=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=2)[CH:17]=[CH:18][CH:19]=1)([CH3:13])([CH3:12])[CH3:11]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 3437981-Bromo-3-tert-butylbenzeneHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 43021752-Chloro-5-methylpyrimidin-4-amine

Product 1

HCID 57516489HCID 57516489, compoundYield 99%

Reagents, catalysts & solvents 2

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

Procedure

A mixture of 2-chloro-5-methylpyrimidin-4-amine (670 mg, 4.7 mmol), 1-tert-butyl-3-bromobenzene (1.5 g, 7 mmol), Pd2(dba)3 (366 mg, 0.4 mmol), Xantphos (695 mg, 1.2 mmol) and cesium carbonate (6.2 g, 19 mmol) was suspended in dioxane (150 mL) and heated at reflux under the argon atmosphere for 20 h. The mixture was filtered and the filtrate concentrated in vacuo. The residue was dissolved in EtOAc (10 mL) and added hexanes (100 mL). The solid was collected by filtration and washed with hexanes to afford the crude title compound (1.2 g, 99%) as a yellow solid.

Workup

  1. temperatureheated
  2. temperatureat reflux under the argon atmosphere for 20 h
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate concentrated in vacuo
  5. dissolutionThe residue was dissolved in EtOAc (10 mL)
  6. additionadded hexanes (100 mL)
  7. filtrationThe solid was collected by filtration
  8. washwashed with hexanes

Sources & evidence

ORD record
ord-2299e06ba08a499a9cde05d2fc718efa
Source dataset
uspto-grants-2009_05
Patent number
US07528143B2

Reaction notes

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