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

HRID 2381389
Notes
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Reaction equation

HRID 2381389 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 668753332-[5-chloro-4-(4,6-dimethyl-pyrimidin-2-yloxy)-6-oxo-6H-pyridazin-1-yl]-3-cyclopentyl-propionic acid methyl ester

Product 1

HCID 668750953-cyclopentyl-2-[4-(4,6-dimethyl-pyrimidin-2-yloxy)-6-oxo-6H-pyridazin-1-yl]-propionic acid methyl esterYield 132.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst
HCID 702
Ethanol
Solvent

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

  1. temperatureThe resulting mixture was refluxed for 30 min
  2. filtrationthe reaction was filtered
  3. washthe solid was rinsed with ethanol
  4. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes