Cesium carbonate → HCID 86617542, compound

HRID 2234351Notes

Reaction equation

HRID 2234351 reaction equation
Br[C:2]1[C:3]([N:9]([CH3:16])[CH2:10][CH2:11][C:12]([NH:14][CH3:15])=[O:13])=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=C3C=2OC2C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=CC=2C3(C)C)C=CC=CC=1.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]>[Cl:8][C:5]1[N:4]=[C:3]2[C:2]([N:14]([CH3:15])[C:12](=[O:13])[CH2:11][CH2:10][N:9]2[CH3:16])=[CH:7][N:6]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 86617566HCID 86617566, compound2×

Product 1

HCID 86617542HCID 86617542, compoundYield 19%

Reagents, catalysts & solvents 2

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

Procedure

3-[(5-Bromo-2-chloro-pyrimidin-4-yl)-methyl-amino]-N-methyl-propanamide (Intermediate 15; 2.09 g, 6.20 mmol), tris(dibenzylideneacetone)dipalladium(0) (171 mg, 0.19 mmol), (5-diphenylphosphanyl-9,9-dimethyl-xanthen-4-yl)-diphenyl-phosphane (288 mg, 0.50 mmol) and Cs2CO3 (2930 mg, 8.99 mmol) in 1,4-dioxane (50 mL) were heated at reflux for 16 h under an atmosphere of nitrogen. The reaction mixture was evaporated then suspended in DCM (20 mL) and filtered through a layer of celite washing with DCM (40 mL). Purification by column chromatography (SiO2, eluent gradient: 2-10% MeOH in DCM) afforded the title compound (190 mg, 19%) as a foam.

Workup

  1. temperatureat reflux for 16 h under an atmosphere of nitrogen
  2. customThe reaction mixture was evaporated
  3. filtrationfiltered through a layer
  4. washof celite washing with DCM (40 mL)
  5. customPurification by column chromatography (SiO2, eluent gradient: 2-10% MeOH in DCM)

Sources & evidence

ORD record
ord-0d65c8e57bbb44bc9d44783a7aeec649
Source dataset
uspto-grants-2010_05
Patent number
US07709471B2

Reaction notes

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