Ammonium formate → 3-cyclopentyl-2-[4-(4,6-dimethyl-pyrimidin-2-yloxy)-6-oxo-6H-pyridazin-1-yl]-propionic acid methyl ester

HRID 2381389Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:28])[CH:4]([N:11]1[C:16](=[O:17])[C:15](Cl)=[C:14]([O:19][C:20]2[N:25]=[C:24]([CH3:26])[CH:23]=[C:22]([CH3:27])[N:21]=2)[CH:13]=[N:12]1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1.C([O-])=O.[NH4+]>C(O)C.[Pd]>[CH3:1][O:2][C:3](=[O:28])[CH:4]([N:11]1[C:16](=[O:17])[CH:15]=[C:14]([O:19][C:20]2[N:25]=[C:24]([CH3:26])[CH:23]=[C:22]([CH3:27])[N:21]=2)[CH:13]=[N:12]1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 2-[5-chloro-4-(4,6-dimethyl-pyrimidin-2-yloxy)-6-oxo-6H-pyridazin-1-yl]-3-cyclopentyl-propionic acid methyl ester (0.37 g, 0.91 mmol) in ethanol (10 mL) was treated with palladium on carbon (0.037 g) and ammonium formate (0.14 g, 2.27 mmol). The resulting mixture was refluxed for 30 min. After cooling to 25° C., the reaction was filtered and the solid was rinsed with ethanol. The filtrate was concentrated in vacuo to afford crude 3-cyclopentyl-2-[4-(4,6-dimethyl-pyrimidin-2-yloxy)-6-oxo-6H-pyridazin-1-yl]-propionic acid methyl ester (0.45 g), which could be further purified by chromatography (5/1 petroleum ether/ethyl acetate).

Workup

temperatureThe resulting mixture was refluxed for 30 min
filtrationthe reaction was filtered
washthe solid was rinsed with ethanol
concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record: ord-5414426ffde84472b17737b84e323268
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08258134B2

Reaction notes

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