ChemicalBook--->CAS DataBase List--->543712-81-8

543712-81-8

543712-81-8 Structure

543712-81-8 Structure
IdentificationBack Directory
[Name]

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

543712-81-8
[Synonyms]

102239
oro-N-(5-methyL
2,5-Dichloro-N-(5-methyl-1H-pyrazol-3-yl)-4-pyrimidinamine
2,5-dichloro-N-(5-Methyl-1H-pyrazol-3-yl)pyriMidin-4-aMine
4-Pyrimidinamine, 2,5-dichloro-N-(5-methyl-1H-pyrazol-3-yl)-
[Molecular Formula]

C8H7Cl2N5
[MDL Number]

MFCD12406889
[MOL File]

543712-81-8.mol
[Molecular Weight]

244.08
Chemical PropertiesBack Directory
[storage temp. ]

under inert gas (nitrogen or Argon) at 2–8 °C
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H302-H315-H319-H332-H335
[Precautionary statements ]

P280-P305+P351+P338-P310
Hazard InformationBack Directory
[Synthesis]

3-Amino-5-methylpyrazole

31230-17-8

2,4,5-Trichloropyrimidine

5750-76-5

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

543712-81-8

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
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