ChemicalBook CAS DataBase List MK-1775

MK-1775 synthesis

5synthesis methods

Product Name:MK-1775
CAS Number:955365-80-7
Molecular formula:C27H32N8O2
Molecular Weight:500.6

2-allyl-1-(6-(2-hydroxypropan-2-yl)pyridin-2-yl)-6-(Methylthio)-1H-pyrazolo[3,4-d]pyriMidin-3(2H)-one

955369-56-9

16153-81-4

955365-80-7

Synthesis of 2-allyl-1-(6-(2-hydroxypropan-2-yl)pyridin-2-yl)-6-(methylmercapto)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one and 4-(4-methyl-1-piperazinyl)aniline using 2-allyl-1-(6-(2-hydroxypropan-2-yl)pyridin-2-yl)-6-(4-(4-methylpiperazin-1- based) phenylamino)-1H-pyrazolo[3,4-D]pyrimidin-3(2H)-one was prepared in the following general procedure: to a 20 mL solution of 1.10 g of 2-allyl-1-(6-(2-hydroxypropan-2- yl)pyridin-2-yl)-6-(methylmercapto)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one in toluene was added 817 mg of isochloroperbenzoic acid ( purity >65%) and the reaction was stirred for 20 minutes. Subsequently, 1.61 mL of N,N-diisopropylethylamine and 706 mg of 4-(4-methylpiperazin-1-yl)aniline were added to the reaction system and the reaction was continued with stirring overnight. After completion of the reaction, saturated aqueous sodium bicarbonate was added to the reaction solution, the organic phase was extracted with ethyl acetate, then the organic phase was washed with saturated brine and finally dried with anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure, and the resulting residue was purified by basic silica gel column chromatography (eluent ratio: hexane/ethyl acetate=1/1~0/1, followed by ethyl acetate/ethanol=98/2). The purified solution was concentrated and recrystallized with ethyl acetate to afford 1.20 g of the target compound 2-allyl-1-(6-(2-hydroxypropan-2-yl)pyridin-2-yl)-6-(4-(4-methylpiperazin-1-yl)phenylamino)-1H-pyrazolo[3,4-D]pyrimidin-3(2H)-one as a yellow solid. The product was confirmed by 1H-NMR (400 MHz, CDCl3) and ESI-MS (m/z [M+H]+ 501) characterization.

26218-75-7 Synthesis

26218-75-7
241 suppliers
$9.00/1g

955365-80-7
237 suppliers
$28.00/1unit

Yield:-

Steps:

Multi-step reaction with 3 steps
1.1: diethyl ether / 0.08 h / 20 °C / Inert atmosphere
2.1: potassium carbonate; N,N`-dimethylethylenediamine; copper(l) iodide / 1,4-dioxane / 18 h / 80 - 95 °C
3.1: 3-chloro-benzenecarboperoxoic acid / toluene / 1 h / 20 °C
3.2: 18 h / 20 °C

References:

Matheson, Christopher J.;Casalvieri, Kimberly A.;Backos, Donald S.;Reigan, Philip [ChemMedChem,2018,vol. 13,# 16,p. 1681 - 1694]

FullText

955369-56-9 Synthesis

955369-56-9
45 suppliers
$287.00/100mg

16153-81-4
314 suppliers
$9.00/250mg

955365-80-7
237 suppliers
$28.00/1unit

References

16153-81-4
314 suppliers
$9.00/250mg

955365-80-7
237 suppliers
$28.00/1unit

References

638218-78-7 Synthesis