Potassium Carbonate → 5-(2-(1H-pyrazol-4-yl)ethoxy)-7-chloro-3-methylpyrido[4,3-d]pyrimidin-4(3H)-one

HRID 1023320Notes

Reaction equation

Cl[C:2]1[C:11]2[C:10](=[O:12])[N:9]([CH3:13])[CH:8]=[N:7][C:6]=2[CH:5]=[C:4]([Cl:14])[N:3]=1.[NH:15]1[CH:19]=[C:18]([CH2:20][CH2:21][OH:22])[CH:17]=[N:16]1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1>[NH:15]1[CH:19]=[C:18]([CH2:20][CH2:21][O:22][C:2]2[C:11]3[C:10](=[O:12])[N:9]([CH3:13])[CH:8]=[N:7][C:6]=3[CH:5]=[C:4]([Cl:14])[N:3]=2)[CH:17]=[N:16]1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 5,7-dichloro-3-methylpyrido[4,3-d]pyrimidin-4(3H)-one (115.0 mg, 0.50 mmol), 2-(1H-pyrazol-4-yl)ethanol (112.1 mg, 1.00 mmol) and K2CO3 (138.2 mg, 1.00 mmol) in 1,4-dioxane (5 mL) was heated at 80° C. overnight, cooled down, quenched with H2O (25 mL) and extracted with EtOAc (3×12.5 mL). The combined organic layer was evaporated under reduced pressure and purified by reverse phase HPLC to afford 5-(2-(1H-pyrazol-4-yl)ethoxy)-7-chloro-3-methylpyrido[4,3-d]pyrimidin-4(3H)-one.

Workup

temperaturecooled down
customquenched with H2O (25 mL)
extractionextracted with EtOAc (3×12.5 mL)
customThe combined organic layer was evaporated under reduced pressure
custompurified by reverse phase HPLC

Sources & evidence

ORD record: ord-271740eadd6e4d47918b841bef7c49ae
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722692B2

Reaction notes

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