Ethylamine → 5-Benzyloxy-2-difluoromethyl-1-ethyl-1H-pyridin-4-one

HRID 1187452Notes

Reaction equation

HRID 1187452 reaction equation
[CH2:1]([O:8][C:9]1[C:10](=[O:18])[CH:11]=[C:12]([CH:15]([F:17])[F:16])O[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:19]([NH2:21])[CH3:20]>CO>[CH2:1]([O:8][C:9]1[C:10](=[O:18])[CH:11]=[C:12]([CH:15]([F:16])[F:17])[N:21]([CH2:19][CH3:20])[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6341EthylamineHCID 598182925-Benzyloxy-2-difluoromethyl-pyran-4-one

Product 1

HCID 672829675-Benzyloxy-2-difluoromethyl-1-ethyl-1H-pyridin-4-oneYield 52%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

5-Benzyloxy-2-difluoromethyl-pyran-4-one (2.0 g, 7.93 mmol) was suspended in 15 mL of methanol. A 2.0M solution of ethylamine in methanol (8.0 mL) was added at room temperature, and the reaction slowly turned into a clear yellow/green solution over 10 min. After 4 h, the reaction mixture was concentrated in vacuo to an oil. The oil was diluted with 10 mL of ethyl acetate and stirred until a solid precipitated out. The solid was collected by suction filtration, thoroughly washed with ether, and dried to afford the title product (1.14 g, 52% yield). HPLC purity (peak area percent) is 97.5% at λ=280 nm using HPLC Method 1 as described above.

Workup

  1. customthe reaction
  2. waitAfter 4 h
  3. concentrationthe reaction mixture was concentrated in vacuo to an oil
  4. additionThe oil was diluted with 10 mL of ethyl acetate
  5. customprecipitated out
  6. filtrationThe solid was collected by suction filtration
  7. washthoroughly washed with ether
  8. customdried

Sources & evidence

ORD record
ord-0a04787aa020491784a9d9fc7e9f977f
Source dataset
uspto-grants-2014_03
Patent number
US08673943B2

Reaction notes

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