ChemicalBook CAS DataBase List 4-PYRIDINECARBOXAMIDINE

4-PYRIDINECARBOXAMIDINE synthesis

5synthesis methods

Product Name:4-PYRIDINECARBOXAMIDINE
CAS Number:33278-46-5
Molecular formula:C6H7N3
Molecular Weight:121.14

1594-57-6
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$11.00/100mg

33278-46-5
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$110.00/50mg

Yield: 25%

Reaction Conditions:

with 1% Pd on activated carbon;ammonium formate;acetic acid for 96 h;Reflux;

Steps:

Pyridine-4-carboximidamide(45l).
Compound 44l (137 mg, 1.0 mmol) was boiled under reflux with Pd/C(1%, 150 mg) and HCOONH₄ (400 mg, 6.3 mmol) in AcOH (5 mL) for 4 d.The suspension was filtered (Celite). The evaporation residue wasbasified with aq. NaOH (5 M, 20 mL) and extracted (EtOAc, 3 ). Evaporation and drying gave 45l (30.5 mg, 25%) as a whitepowder: mp >200°C (decomp.) (lit.³³ 235-238°C); ¹HNMR d7.78 (2 H, d, J = 5.5 Hz, 3,5-H₂),8.87 (2 H, d, J = 5.0 Hz, 2,6-H₂),9.52 (3 H, br, NH and NH₂); ¹³C NMR d 121.39 (3,5-C₂), 141.24 (4-C), 150.24(2,6-C₂), 166.38 (C=N); MS m/z122.0710 (M + H)⁺ (C₆H₈N₃ requires122.0718).

References:

Kumpan, Katerina;Nathubhai, Amit;Zhang, Chenlu;Wood, Pauline J.;Lloyd, Matthew D.;Thompson, Andrew S.;Haikarainen, Teemu;Lehti?, Lari;Threadgill, Michael D. [Bioorganic and Medicinal Chemistry,2015,vol. 23,# 13,art. no. 12299,p. 3013 - 3032] Location in patent:supporting information

100-48-1 Synthesis