ChemicalBook CAS DataBase List Pyrazinamine, 5-phenyl-3-(phenylmethyl)-

Pyrazinamine, 5-phenyl-3-(phenylmethyl)- synthesis

10synthesis methods

Product Name:Pyrazinamine, 5-phenyl-3-(phenylmethyl)-
CAS Number:70217-86-6
Molecular formula:C17H15N3
Molecular Weight:261.32

174680-55-8 Synthesis

2-AMINO-3-(PHENYLMETHYL)-5-BROMOPYRAZINE

174680-55-8
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98-80-6 Synthesis

98-80-6
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$5.00/5g

Pyrazinamine, 5-phenyl-3-(phenylmethyl)-

70217-86-6
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Yield:70217-86-6 92%

Reaction Conditions:

with [1,4-bis(diphenylphosphino)butane] palladium(ll) dichloride;cis-dichlorobis(benzonitrile)palladium(II);sodium carbonate in ethanol;water;toluene at 105; for 5 h;Inert atmosphere;

Steps:

Synthesisof 3-benzyl-5-phenylpyrazine-2-amine (6).

3-Benzyl-5-bromopyrazine-2-amine (5) (1.32g, 5 mmol, 1 eq.) and phenylboronic acid (915 mg, 7.5 mmol, 1.5 eq.) were dissolved in toluene (70 mL) and stirred at room temperature. Ethanol (20 ml) and 1 M Na₂CO₃ aq. (48 mL) were added to the reaction mixture. After vacuum deaeration and argon gas protection, 1,4-bis(diphenylphosphino)butane-palladium(II)chloride (190 mg, 0.31 mmol, 14% of compound 5) and bis(benzonitrile)palladium(II)chloride (120 mg, 0.31 mmol, 9% of compound 5) in 30 mL of toluene was added into the solution and the mixture was deaerated again and stirred for 5 hours at 105 °C under argon atmosphere. After cooling to room temperature, the solution was filtered through a diatomite pad to remove the palladium catalyst. The solution was extracted with ethyl acetate, and the brown organic phase was washed with water and brine, dried over Na₂SO₄ and evaporated. The resulting residue was purified by silica gel column chromatography using petroleum ether/ethyl acetate = 2/1 (v/v), affording 3-benzyl-5-phenylpyrazine-2-amine(6) as a yellow solid (1.2 g, 92%). ¹H NMR (300 MHz, DMSO-d₆): δ 8.43 (s,1H), 7.92-7.90(2H, t, J = 6.9 Hz), 7.43-7.39 (2H,t, J = 7.2 Hz), 7.36-7.25 (5H, m),7.21-7.18 (1H, t, J = 5.0 Hz), 6.42(2H, s), 4.09 (2H, s); ESI-MS calcd. for C₁₇H₁₅N₃: 261.1, found: 262.0 (M+H⁺).

References:

Yuan, Ming-Liang;Jiang, Tian-Yu;Du, Lu-Pei;Li, Min-Yong [Chinese Chemical Letters,2016,vol. 27,# 4,p. 550 - 554] Location in patent:supporting information

2-Pyrazinamine, 5-phenyl-3-(phenylmethyl)-, 1-oxide

196959-78-1
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70217-86-6
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References

93554-83-7 Synthesis

2-AMINO-3-PHENYLPROPIONITRILE HYDROCHLORIDE

93554-83-7
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70217-86-6
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References

Methanesulfonic acid, 1,1,1-trifluoro-, 5-[[(4-methylphenyl)sulfonyl]amino]-6-(phenylmethyl)-2-pyrazinyl ester

671240-61-2
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70217-86-6
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Benzenesulfonamide, 4-methyl-N-[5-phenyl-3-(phenylmethyl)-2-pyrazinyl]-

671240-62-3
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70217-86-6
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References