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Einecs 211-027-4 → CID 117760255

HRID 709610
Notes
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Reaction equation

HRID 709610 reaction equation
[CH:1]1([CH:4]([C:11]2[CH:16]=[C:15]([O:17]C)[N:14]=[CH:13][N:12]=2)[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:3][CH2:2]1.[Cl-].[NH+]1C=CC=CC=1.C(=O)([O-])O.[Na+]>CN(C=O)C.C(#N)C>[CH:1]1([CH:4]([C:11]2[CH:16]=[C:15]([OH:17])[N:14]=[CH:13][N:12]=2)[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:3][CH2:2]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 69401Einecs 211-027-4HCID 516892Sodium BicarbonateHCID 117760142Ethyl 3-cyclopropyl-3-(6-methoxypyrimidin-4-yl)propanoate

Product 1

HCID 178471101CID 117760255

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342
Acetonitrile
Solvent

Conditions

Temperature
130 °C

Procedure

Under a nitrogen atmosphere, to a solution of ethyl 3-cyclopropyl-3-(6-methoxypyrimidin-4-yl)propanoate (entire amount) in DMF (15 mL) was added pyridinium chloride (25.9 g), and the mixture was stirred at 130° C. for 20 min. The reaction mixture was cooled to 0° C. and diluted with acetonitrile (20 mL). Sodium hydrogen carbonate (17.0 g) was added to the reaction mixture, the insoluble material was filtered off, and the solvent in the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane), and the obtained solid was washed with diisopropyl ether to give the title compound (3.66 g) as a white solid.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. filtrationthe insoluble material was filtered off
  3. customthe solvent in the filtrate was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)
  5. washthe obtained solid was washed with diisopropyl ether

Sources & evidence

ORD record
ord-e6dc28229f74484fa35d70feccfd64c6
Source dataset
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09181186B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes