(5,7-dimethyl-3H-8lambda~5~-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methanol

(5,7-dimethyl-3H-8lambda~5~-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methanol Property

Density 

1.42±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

pka

12.76±0.10(Predicted)

Safety

HS Code 

2933998090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H312Harmful in contact with skin

H332Harmful if inhaled

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P322Specific measures (see …on this label).

P330Rinse mouth.

P363Wash contaminated clothing before reuse.

P501Dispose of contents/container to..…

(5,7-dimethyl-3H-8lambda~5~-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methanol Chemical Properties,Usage,Production

Synthesis

The general procedure for the synthesis of (5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methanol from (5-amino-1H-1,2,4-triazol-3-yl)methanol ethanolate and acetylacetone is as follows: refer to the literature method (Lippman, E.; Becker, V., Z. CHEM., 1974, 14, 405 ) with slight modifications: (5-amino-1H-1,2,4-triazol-3-yl)methanol ethanolate (30.7 g, 0.161 mol, from step 1 above) and 2,4-pentanedione (32.3 g, 0.323 mol, 2 eq.) were dissolved in a solvent mixture of ethanol (750 mL) and acetic acid (250 mL) and the reaction was carried out at reflux for 20 hours. At the beginning of the reaction, the mixture was a clarified solution, which gradually turned yellow as the reaction progressed. After completion of the reaction, the solvent was removed by distillation under reduced pressure to obtain a yellow paste. Ethanol (100 mL) was added to the paste, ground and stirred for 15 minutes. The paste was cooled to 5 °C (ice bath), stirring was continued for 30 min, filtered and washed with cold (0-5 °C) ethanol. The product was dried under vacuum at 25-30 °C to give 24 g (83.7% yield). The product was confirmed by 1H NMR (300 MHz, DMSO-D6): δ 2.57 (3H, s), 2.71 (3H, s), 4.63 (2H, s), 5.5 (1H, br s, OH), 7.13 (1H, s). analysis by LC-MS (APCI): the calculated value of C8H10N4O (M+H+) was 178.19; measured value (M+H+) was 179.1 m/z.

References

[1] Patent: WO2004/74270, 2004, A2. Location in patent: Page 300-301
[2] Patent: US2005/176701, 2005, A1. Location in patent: Page/Page column 144
[3] Organic Process Research and Development, 2006, vol. 10, # 4, p. 814 - 821
[4] Patent: WO2012/83105, 2012, A1. Location in patent: Page/Page column 102-103
[5] Patent: WO2007/23381, 2007, A1. Location in patent: Page/Page column 55