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ChemicalBook CAS DataBase List Pyrido[2,3-d]pyrimidin-7(8H)-one, 2-amino-8-cyclopentyl-4-methyl-6-(1H-pyrazol-4-yl)-
1013098-90-2

Pyrido[2,3-d]pyrimidin-7(8H)-one, 2-amino-8-cyclopentyl-4-methyl-6-(1H-pyrazol-4-yl)- synthesis

3synthesis methods
552846-17-0 Synthesis
1-Boc-pyrazole-4-boronic acid pinacol ester

552846-17-0
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2-amino-6-bromo-8-cyclopentyl-4-methylpyrido[2,3-d]pyrimidin-7(8H)-one

934495-31-5
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Pyrido[2,3-d]pyrimidin-7(8H)-one, 2-amino-8-cyclopentyl-4-methyl-6-(1H-pyrazol-4-yl)-

1013098-90-2
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Yield:1013098-90-2 65%

Reaction Conditions:

with potassium carbonate;bis-triphenylphosphine-palladium(II) chloride in N,N-dimethyl-formamide at 120; for 0.166667 h;Microwave irradiation;

Steps:

5

Example 5. Preparation of 2-amino-8-cvclopentyl-6-(1 H-pyrazol-4-yl)-4-methylpyridof2,3-Qipyrimidin- 7(8H)-one (Compound 101 ); To a solution of 2-amino-6-bromo-8-cyclopentyl-4-methylpyrido[2,3-c(lpyrimidin-7(8/-/)-one (100 mg, 0.31 mmol), terf-butyl 4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 H-pyrazole-1-carboxy late ( 110 mg, 1.2 equiv), dichlorobis(triphenylphosphine)palladium(ll) (6.5 mg, 009 mmol), DMF (2 ml_) in a 10 mL microwave vial was added potassium carbonate (3 M, 0.8 ml_). The solution was degassed with N2 for 10 min before being capped and heated in the microwave reactor for 10 min at 120 0C. Once complete, the reaction was diluted with 1 N NaOH (10 mL) and EtOAc (50 mL). The EtOAc layer was washed with 3N HCI, dried over MgSO4, filtered, and concentrated under reduced pressure. The crude product was submitted for chromatography purification, the title compound was obtained in (62.5 mg, 65% yield). LRMS: 311 (M+H)+.1H NMR (DMSO-CC6, 400 MHz): 8.26 (2H, bs), 8.13 (1 H, s), 7.09 (2H, bs), 6.04-5.99 (1 H, m), 2.59 (3H, s), 2.27-2.23 (2H1 bm), 2.04 (2H, bm), 1.77-1.74 (2H, bm), 1.62 (2H, bm).

References:

WO2008/32162,2008,A1 Location in patent:Page/Page column 36-37

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