2,5-Dichloro-N-(5-methyl-1H-pyrazol-3-yl)-4-pyrimidinamine

2,5-Dichloro-N-(5-methyl-1H-pyrazol-3-yl)-4-pyrimidinamine Property

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H332Harmful if inhaled

H335May cause respiratory irritation

Precautionary statements

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

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P310Immediately call a POISON CENTER or doctor/physician.

2,5-Dichloro-N-(5-methyl-1H-pyrazol-3-yl)-4-pyrimidinamine Chemical Properties,Usage,Production

Synthesis

The general procedure for the synthesis of 2,5-dichloro-N-(5-methyl-1H-pyrazol-3-yl)-4-aminopyrimidine from 3-amino-5-methyl-1H-pyrazole and 2,4,5-trichloropyrimidine was as follows: to a solution of 5-methyl-1H-pyrazol-3-amine (4.00 g, 41.2 mmol) in anhydrous ethanol (100 mL) was added triethylamine (12.51 g (123.6 mmol) and 2,4,5-trichloropyrimidine (7.56 g, 41.2 mmol). The reaction mixture was stirred at room temperature for 16 h and subsequently concentrated under vacuum. The residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate, v/v = 1/1) to afford the target compound 2,5-dichloro-N-(5-methyl-1H-pyrazol-3-yl)-4-aminopyrimidine as a light yellow solid (9.00 g, 89.5% yield). Mass spectrum (ESI, positive ion mode) m/z: 244.1 [M + H]+; NMR hydrogen spectrum (600 MHz, DMSO-d6) δ (ppm): 12.32 (broad single peak, 1H), 9.70 (single peak, 1H), 8.33 (single peak, 1H), 6.28 (single peak, 1H), 2.25 (single peak, 3H).

References

[1] Journal of Medicinal Chemistry, 2011, vol. 54, # 1, p. 262 - 276
[2] Organic Process Research and Development, 2013, vol. 17, # 9, p. 1123 - 1130
[3] Patent: WO2015/94803, 2015, A1. Location in patent: Paragraph 323
[4] Patent: CN104672250, 2017, B. Location in patent: Paragraph 0762; 0763; 0764; 0765
[5] Patent: EP2754659, 2014, A1. Location in patent: Paragraph 0061-0063