6-(HYDROXYMETHYL)NICOTINONITRILE Chemical Properties

Boiling point:

303.1±32.0 °C(Predicted)

Density 

1.25±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

pka

13.06±0.10(Predicted)

Appearance

Off-white to light yellow Solid

Safety Information

HS Code 

2933399990

6-(HYDROXYMETHYL)NICOTINONITRILE Usage And Synthesis

Uses

6-(Hydroxymethyl)nicotinonitrile is the derivative of 5-Cyano-2-methylpyridine (C981875), which is used to synthesize acridone-based inhibitors of inosine 5''-monophosphate dehydrogenase (IMPDH). It is also used in the preparation of potent and selective nonpeptidic inhibitors of procollagen C-proteinase.This compound is suitable for pyruvate dehydrogenase (PDH) related research.

Synthesis

The general procedure for synthesizing 6-hydroxymethylpyridine-3-carbonitrile from the compound (CAS: 31795-60-5) was as follows: the compound of Example 31A (180 mg, 1.02 mmol) was dissolved in tetrahydrofuran (8 mL). Lithium hydroxide (48.94 mg, 2.04 mmol) was dissolved in water (5 mL) and this aqueous solution was added to the tetrahydrofuran solution. The reaction mixture was stirred at room temperature for 2 hours. After completion of the reaction, the mixture was diluted with water and ethyl acetate. The aqueous phase was extracted three times with ethyl acetate. The organic phases were combined, washed with saturated brine, dried over magnesium sulfate monohydrate, filtered and concentrated in vacuum. The resulting residue was used in the next reaction without further purification. Yield: 125 mg (91% yield). HPLC (Method 8): retention time (Rt) = 1.17 min. mass spectra (DCI): m/z 152 ([M + NH4]+). 1H-NMR (300 MHz, DMSO-d6): δ = 4.63 (d, 2H); 5.64 (t, 1H); 7.65 (d, 1H); 8.29 (dd, 1H); 8.92 (d, 1H) ppm.

References

[1] Patent: WO2004/20412, 2004, A1. Location in patent: Page 47

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