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2-Amino-4-cyanopyridine

2-Amino-4-cyanopyridine structure

CAS No:
42182-27-4
Formula:
C6H5N3
Chemical Name:
2-Amino-4-cyanopyridine
Synonyms:
4-PYRIDINECARBONITRILE, 2-AMINO-;2-AMINO-4-CYANOPYRIDINE;2-Aminoisonicotinonitrile;4-Cyano-2-pyridinamine;5-AMINO-4-CYANOPYRIDINE;2-Amino-4-pyridinecarbonitrile;2-aminopyridine-4-carbonitrile;2-Amino-4-cyanopyrid
Categories:
Pharmaceutical Intermediates > Heterocyclic Compound

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Description

Yellow or pale brown cryst powder

2-Amino-4-cyanopyridine Basic Attributes

Molecular Weight：

119.12

Exact Mass：

119.048347

BRN：

386393

EC Number：

-0

HScode：

2933399090

Characteristics

PSA：

62.7

XLogP3：

0.2

Density：

1.2±0.1 g/cm3

Melting Point：

146-148°C

Boiling Point：

297.7°C at 760 mmHg

Flash Point：

133.8±21.8 °C

Refractive Index：

1.595

Water Solubility：

Slightly soluble in water.

Safety Information

Packing level：

III

Hazard category：

6.1

Transport codes：

3439

hazard class code：

20/21/22-36/37/38-41-37/38-22

safety instructions：

26-36/37/39-36-39

Marks：

Xi,Xn

Precautionary statement(s)：

P261, P264, P270, P271, P280, P301+P310, P302+P352, P304+P340, P305+P351+P338, P311, P312, P321, P322, P330, P332+P313, P337+P313, P361, P362, P363, P403+P233, P405, P501

Hazard Statements：

H301+H311+H331

2-Amino-4-cyanopyridine Use and Manufacturing

Methods of Manufacturing

A mixture of 4-bromopyridin-2-amine (4.9 g, 28.5 mmol), Zn(CN)2 (5.0 g, 42.5 mmol), Pd2(dba)3 (1.3g, 1.4 mmol) and dppf (1.6 g, 2.8 mmol) in DMF (150 mL) was stirred at 100 °C under nitrogen atmosphere for 1.5 h.The mixture was cooled to rt and water (500 mL) was added. The mixture was extracted with EtOAc (300 mL3 3). Thecombined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure.The residue was purified by silica gel chromatography eluting with 10: 1 to 2: 1 petroleum ether/EtOAc to afford 2-aminoisonicotinonitrile as a light yellow solid (2.7 g, 80percent). 1H NMR (300 MHz, CDCl3) δ 8.19 (d, J = 5.1 Hz, 1H), 6.82(d, J = 4.8 Hz, 1H), 6.69 (d, J = 0.9 Hz, 1H), 4.72 (br s, 2H). LCMS (ESI) m/z 120 (M+H)+.A suspension of the product of Step A (4 g, 18.2 mmol) and anhydrous CuCN (1 .82 g, 20.3 mmol) in anhydrous pyridine (5 ml) was refluxed for 30 min. The solvent was removed in vacuo and the residue was partitioned between EtOAc (150 ml) and 10percent NH4CI (pH ~ 9, adjusted with NH40H; 50 ml). The organic phase was washed with brine, dried over anhydrous MgS04, filtered and the filtrate evaporated to dryness to give the title compound (1 .8 g, 82percent), as yellowish solid. STR18 2-Amino-4-cyanopyridine 2-Amino-4-pyridinecarboxamide was dehydrated according to the method of Deady et al. (Aust. J. Chem., 35, 2025 (1982)) to form the title compound (mp. 148-9° C.).

Uses

A pyridine derivative as mGluR2 antagonists; used in the treatment of CNS disorders.

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