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4-[[4-[[4-(2-cyanoethenyl)-2,6-dimethylphenyl]amino]-2-pyrimidinyl]amino]benzonitrile[ No CAS ]
[ 500287-72-9 ]
Yield
Reaction Conditions
Operation in experiment
5%; 7%
A mixture of (cyanomethyl)triphenylphosphonium chloride (0.0022 mol) and potassium tert.-butoxide (0.0022 mol) in THF (7 ml) was stirred at 5 C. for 30 minutes under N2 flow, then stirred at 5 C. for 30 minutes. A mixture of intermediate 13 (0.0015 mol) in THF (7 ml) was added. The mixture was stirred for 8 hours in darkness, poured out into H2O and extracted with CH2Cl2. The organic layer was separated, dried (MgSO4), filtered and the solvent was evaporated. The residue (1.4 g) was purified by column chromatography over silica gel (eluent: toluene/iPrOH/NH4OH 96/4/0.1; 15-40 mum). Two fractions (F1, F2) were collected and the solvent was evaporated. Yield: 0.165 g of F1 (E/Z=32/68) (30%) and 0.225 g of F2 (E/Z=0/10) (41%). F2 was crystallized from CH3CN/diethyl ether. Yield: 0.036 g of compound 1 (7%). F1 was purified by column chromatography over kromasyl (eluent: toluene/iPrOH 98/2; 5 mum). The pure fractions were collected and the solvent was evaporated. Yield: 0.029 g of compound 10 (5%).
4-[[4-[[4-(2-cyanoethenyl)-2,6-dimethylphenyl]amino]-2-pyrimidinyl]amino]benzonitrile[ No CAS ]
[ 500287-72-9 ]
Yield
Reaction Conditions
Operation in experiment
55%
With triethylamine; tris-(o-tolyl)phosphine;palladium diacetate; In acetonitrile; at 150℃;
A mixture of intermediate (IV-a) (0.00021 mol), prepared according to Example A4, acrylonitrile (CH2=CH-CN) (0.00213 mol), Pd (OAc) 2 (0.000043 mol), N,N-diethylethanamine (0.000043 mol) and tris (2-methylphenyl) phosphine (0.00021 mol) in CH3CN (7 ml) was stirred in a sealed vessel at 150C overnight. H20 was added. The mixture was extracted with CH2C12. The organic layer was separated, dried (MgS04), filtered and the solvent was evaporated. The residue (0.15 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/ethyl acetate 80/20; 15-40 mum). Fraction 1 was collected and the solvent was evaporated, yielding 0.045g of 4-[[4-[[4- [(2-cyanoethenyl)-2,6-dimethylphenyl] amino]-2-pyrimidinyl]amino] benzonitrile (E/Z=80/20). The solid was crystallized from diethylether. Yield: 0.035g of 4-[[4-[[4- (2-cyanoethenyl)-2, 6-dimethylphenyl] amino]-2-pyrimidinyl] amino] benzonitrile (E) (Compound X) [(55%).]
With palladium diacetate; triethylamine; tris-(o-tolyl)phosphine; In acetonitrile; at 150℃;Sealed tube;
A mixture of intermediate 58 (0.00021 mol), prepared according to Example A11, acrylonitrile (CH2?CH-CN) (0.00213 mol), Pd(OAc)2 (0.000043 mol), N,N-diethylethanamine (0.000043 mol) and tris(2-methylphenyl)phosphine (0.00021 mol) in CH3CN (7 ml) was stirred in a sealed vessel at 150 C. overnight H2O was added. The mixture was extracted with CH2Cl2. The organic layer was separated, dried (MgSO4), filtered and the solvent was evaporated. The residue (0.15 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/ethyl acetate 80/20; 15-40 mum). Fraction 1 was collected and the solvent was evaporated, yielding 0.045 g of 4-[[4-[[4-(2-cyanoethenyl)-2,6-dimethylphenyl]amino]-2-pyrimidinyl]amino]benzonitrile (E/Z=80/20). The solid was crystallized from diethylether. Yield: 0.035 g of 4-[[4-[[4-(2-cyanoethenyl)-2,6-dimethylphenyl]amino]-2-pyrimidinyl]amino]benzonitrile (E) (compound 1) (55%).
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