Cesium carbonate → (4-{1-[(2-Methoxy-6-phenyl-pyrimidin-4-yl)-hydrazono]-ethyl}-phenyl)-dimethylamine

HRID 2063607Notes

Reaction equation

HRID 2063607 reaction equation
Cl[C:2]1[N:7]=[C:6]([O:8][CH3:9])[N:5]=[C:4]([NH:10][N:11]=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([N:20]([CH3:22])[CH3:21])=[CH:16][CH:15]=2)[CH3:13])[CH:3]=1.[C:23]1(B(O)O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[Cl-].CC1C=C(C)C=C(C)C=1[N+]1C=CN(C2C(C)=CC(C)=CC=2C)C=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]>[CH3:9][O:8][C:6]1[N:5]=[C:4]([NH:10][N:11]=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([N:20]([CH3:22])[CH3:21])=[CH:16][CH:15]=2)[CH3:13])[CH:3]=[C:2]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:7]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 66827Phenylboronic AcidHCID 27342111,3-Bis(2,4,6-trimethylphenyl)imidazolium chlorideHCID 72577512(4-{1-[(6-Chloro-2-methoxy-pyrimidin-4-yl)hydrazono]-ethyl}-phenyl)-dimethylamine

Product 1

HCID 73320053(4-{1-[(2-Methoxy-6-phenyl-pyrimidin-4-yl)-hydrazono]-ethyl}-phenyl)-dimethylamine

Reagents, catalysts & solvents 2

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

Procedure

The title compound was prepared from (4-{1-[(6-chloro-2-methoxy-pyrimidin-4-yl)hydrazono]-ethyl}-phenyl)-dimethylamine (100 mg, 0.31 mmol), phenyl boronic acid (190 mg, 1.6 mmol), 1,3-bis(2,4,6-trimethylphenyl)imidazolium chloride (15 mg, 0.04 mmol), tris(dibenzylideneacetone)dipalladium (20 mg, 0.02 mmol) and cesium carbonate (611 mg, 1.9 mmol) in 1,4-dioxane (3 mL) by a procedure similar to Example 9, Step 3 yielding 61 mg (54%) of a yellow solid. HPLC Purity: 92%.

Sources & evidence

ORD record
ord-b2dc13f7086640209e5f89d396287d2a
Source dataset
uspto-grants-2012_10
Patent number
US08288398B2

Reaction notes

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