- Direct access to 2-(N-alkylamino)pyrimidines via ruthenium catalyzed tandem multicomponent annulation/N-alkylation
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2-(N-alkylamino)pyrimidines are important heterocycles widely found in various pharmaceutically important drugs. Here, we have disclosed a new cooperative ruthenium complex catalyzed tandem multicomponent synthesis of 2-(N-alkylamino)pyrimidines directly from guanidine salt and alcohols. The reactions proceeded through the dehydrogenation of alcohols, followed by C[sbnd]C coupling and sequential C[sbnd]N coupling with guanidine and primary alcohol, with the elimination of three equivalents of hydrogen gas. In this work, application of both the acceptorless dehydrogenative coupling (ADC) and borrowing hydrogen (BH) strategies were accomplished in a single reaction. This catalytic method tolerated a wide range of substrates. The viability of the current method was demonstrated by preparative scale synthesis of a few products. A plausible catalytic cycle was proposed based on various control experiments, mechanistic studies and DFT calculations. Remarkably, 42 new 2-(N-alkylamino)pyrimidines were synthesized following this catalytic protocol.
- Borthakur, Ishani,Guria, Saikat,Kundu, Sabuj,Maji, Milan,Singha, Suman
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- Regioselective N-alkylation with alcohols for the preparation of 2-(N-alkylamino)quinazolines and 2-(N-alkylamino)pyrimidines
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In the presence of the [Cp*IrCl2]2/NaOH system, the direct N-alkylation of 2-aminoquinazolines and 2-aminopyrimidines with alcohols afforded the N-exosubstituted 2-(N-alkylamino)quinazolines and 2-(N-alkylamino)pyrimidines with 71-96
- Li, Feng,Chen, Lin,Kang, Qikai,Cai, Jianguang,Zhu, Guangjun
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p. 624 - 631
(2013/03/28)
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- One-pot two-step solvent-free rapid and clean synthesis of 2-(substituted amino)pyrimidines by microwave irradiation
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abs A series of diversely 2-(substituted amino)pyrimidines (along with ring substitution) has been synthesized under solvent- and catalyst-free microwave conditions from substituted guanidines and β-diketones. The substituted guanidines are synthesized from (S)-methylisothiourea sulfate and different amines (various alkyl, aryl, or heterocyclic and also chiral amines) under microwave irradiation. These two-step reactions are performed in one-pot without isolating any intermediate. This protocol has been successfully applied for the synthesis of bisaminopyrimidines and 2-substituted aminopyrimidines containing chiral moiety where chirality remains undisturbed.
- Goswami, Shyamaprosad,Hazra, Anita,Jana, Subrata
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experimental part
p. 1175 - 1181
(2009/12/25)
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- Metallation Studies with Pyrimidines
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2-Alkylamino-4,6-diphenylpyrimidines are acylated only at nitrogen after treatment with lithium di-isopropylamide (LDA). 4,6-Diaryl-1-benzylpyrimidin-2(1H)-ones can be acylated and alkylated at the α-CH3 group. 1-Methyl-4,6-di-p-tolylpyrimidin-2(1H)-one f
- Katrizky, Alan R.,Salgado, Hector J.,Chermprapai, Amornsri,Ponkshe, Narayan K.
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p. 153 - 158
(2007/10/02)
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