Methyl 5-aminopyrazine-2-carboxylate

Methyl 5-aminopyrazine-2-carboxylate (CAS 13924-94-2) is a strategically bifunctional pyrazine ester engineered for heterocyclic diversification, pharmaceutical intermediate synthesis, and antifolate drug development. This molecule integrates an electron-deficient pyrazine core—a six-membered aromatic diazine ring with nitrogen atoms at para positions (1,4)—with an amino substituent at the C5 position and a methyl ester group at the C2 position. The C2-ester moiety serves as a versatile handle for hydrolysis to the free acid, transesterification, or direct amidation, while the C5-amino group provides orthogonal reactivity for acylation, alkylation, diazotization, or heterocyclic fusion. Compared to its carboxylic acid analog (CAS 40155-43-9), the methyl ester form offers enhanced lipophilicity, improved membrane permeability for cellular assays, and simplified purification protocols. This dual-functionality architecture is particularly valuable for constructing fused heterocycles (pyrazino-fused systems), kinase inhibitor cores, antimetabolite analogs (e.g., methotrexate derivatives), and prodrug architectures where the aminoester-pyrazine motif balances synthetic flexibility with tunable physicochemical properties. Manufactured with purity ≥98% under controlled conditions, it supports drug discovery programs requiring modular access to functionalized diazine architectures with orthogonal derivatization pathways.

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Product Name	Methyl 5-aminopyrazine-2-carboxylate
CAS Number	13924-94-2
Chinese Name	5-氨基吡嗪 -2-羧酸甲酯
Synonyms	Methyl 5-amino-2-pyrazinecarboxylate; Pyrazine-2-carboxylic acid, 5-amino-, methyl ester; C₆H₇N₃O₂ heterocycle; Methyl 5-APCA
Chinese Synonyms	5-氨基 -2-吡嗪羧酸甲酯; 5-氨基吡嗪 -2-甲酸甲酯; 氨基吡嗪羧酸甲酯; 5-位氨基 -2-位甲酯吡嗪
Molecular Formula	C₆H₇N₃O₂
Molecular Weight	153.15 g/mol
Purity	≥ 98% (HPLC area normalization)
Product Category	Pharmaceutical Intermediates / Pyrazine Derivatives / Amino Ester Heterocycles
Appearance	Light tan to orange solid
Melting Point	~165-170°C (literature reference recommended)
Storage Conditions	Store in a cool, dry, well-ventilated area away from light and moisture. Keep container tightly closed under inert atmosphere (nitrogen). Protect from strong bases to avoid ester hydrolysis and from strong oxidizing agents to avoid amino group oxidation.
Shelf Life	24 months under recommended storage conditions
Packaging	100mg/vial, 500mg/vial, 1g/bottle, 5g/bottle, or customized according to customer requirements
Applications	Kinase inhibitor synthesis, antifolate drug development (methotrexate analogs), heterocyclic library construction (pyrazino-fused systems), prodrug design via ester hydrolysis, amide coupling for drug conjugates, ligand synthesis for coordination chemistry
Reactivity	Suitable for amino group acylation/alkylation, ester hydrolysis to acid, transesterification, heterocyclic fusion, electrophilic aromatic substitution at C3/C6, and salt formation (after hydrolysis)
Special Note	✅ Bifunctional Amino Ester Scaffold—C2-COOMe for hydrolysis/coupling, C5-NH₂ for derivatization. Enhanced lipophilicity vs. free acid analog (CAS 40155-43-9). Part of our pyrazine building block series.