Ethyl 3-cyclopropyl-3-(6-methoxypyrimidin-4-yl)acrylate → Ethyl 3-cyclopropyl-3-(6-methoxypyrimidin-4-yl)propanoate

HRID 709609Notes

Reaction equation

HRID 709609 reaction equation
[CH:1]1([C:4]([C:11]2[CH:16]=[C:15]([O:17][CH3:18])[N:14]=[CH:13][N:12]=2)=[CH:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:3][CH2:2]1>C(O)(=O)C.[Zn]>[CH:1]1([CH:4]([C:11]2[CH:16]=[C:15]([O:17][CH3:18])[N:14]=[CH:13][N:12]=2)[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:2][CH2:3]1

Participants

4

Reactant 1

HCID 131733897Ethyl 3-cyclopropyl-3-(6-methoxypyrimidin-4-yl)acrylate

Product 1

HCID 117760142Ethyl 3-cyclopropyl-3-(6-methoxypyrimidin-4-yl)propanoateYield 101.2%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

A zinc powder (11.5 g) was added to a solution of ethyl 3-cyclopropyl-3-(6-methoxypyrimidin-4-yl)acrylate (5.57 g) in acetic acid (60 mL), and the mixture was stirred at room temperature for 10 min. The reaction mixture was filtered, and the solvent in the filtrate was evaporated under reduced pressure to give a crude product of the title compound (5.68 g) as a yellow oil. This compound was used for the next step without further purification.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe solvent in the filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-abbb7df315a44e54bed93d72a6f26efb
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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