2-[4-(6-AMINO-2-METHYLPYRIMIDIN-4-YL)PIPERAZIN-1-YL]ETHANOL

2-[4-(6-AMINO-2-METHYLPYRIMIDIN-4-YL)PIPERAZIN-1-YL]ETHANOL Property

Melting point:

187-188 °C

Boiling point:

465.7±45.0 °C(Predicted)

Density 

1.230

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

14.96±0.10(Predicted)

Safety

HS Code 

2933399990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H317May cause an allergic skin reaction

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

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

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.

2-[4-(6-AMINO-2-METHYLPYRIMIDIN-4-YL)PIPERAZIN-1-YL]ETHANOL Chemical Properties,Usage,Production

Synthesis

General procedure for the synthesis of 2-(4-(6-amino-2-methylpyrimidin-4-yl)piperazin-1-yl)ethanol from N-hydroxyethylpiperazine and 2-methyl-4-amino-6-chloropyrimidine: 6-chloro-2-methylpyrimidin-4-ylamine (500 mg, 3.49 mmol), N-hydroxyethylpiperazine (500 mg, 3.84 mmol) and N,N-di isopropylethylamine (DIPEA, 541 mg, 4.19 mmol) were dissolved in 1,4-dioxane (5 mL). The reaction mixture was heated to reflux for 12 hours. The progress of the reaction was monitored by thin layer chromatography (TLC) and after confirming the completion of the reaction, the reaction mixture was concentrated. The residue was washed with acetonitrile (MeCN) and subsequently recrystallized from methanol (MeOH) to afford the target compound 2-[4-(6-amino-2-methylpyrimidin-4-yl)piperazin-1-yl]ethanol (220 mg, 26.5% yield) as a white solid.1H NMR (400 MHz, MeOD) data were as follows: δ 5.61 (s, 1H, ArH), δ 3.74 (t, J = 6.0 Hz, 2H, OCH2), 3.64-3.61 (m, 4H, 2×CH2), 2.67-2.62 (m, 6H, 3×CH2), 2.31 (s, 3H, ArCH3).

References

[1] Tetrahedron Letters, 2009, vol. 50, # 41, p. 5729 - 5732
[2] Patent: WO2014/52365, 2014, A1. Location in patent: Page/Page column 174-175