N-(1-(5-Fluoropyrimidin-2-yl)vinyl)acetamide → HCID 58367416, compound

HRID 75950Notes

Reaction equation

HRID 75950 reaction equation
[F:1][C:2]1[CH:3]=[N:4][C:5]([C:8]([NH:10][C:11](=[O:13])[CH3:12])=[CH2:9])=[N:6][CH:7]=1>CO>[F:1][C:2]1[CH:7]=[N:6][C:5]([C@@H:8]([NH:10][C:11](=[O:13])[CH3:12])[CH3:9])=[N:4][CH:3]=1

Participants

3

Reactant 1

HCID 45119272N-(1-(5-Fluoropyrimidin-2-yl)vinyl)acetamide

Product 1

HCID 58367416HCID 58367416, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-(1-(5-Fluoropyrimidin-2-yl)vinyl)acetamide (Method 58, 0.10 g, 0.55 mmol) in MeOH (5 ml) under N2 was added (+)-1,2-bis((2S,5S)-2,5-diethylphospholano)benzene (cyclooctadiene)rhodium(I)trifluoromethanesulfonate (0.04 g, 0.0055 mmol). The solution was transferred to a high pressure bomb and charged 150 psi H2. The reaction stirred at room temperature for 4 hours. The solvent was removed and the resulted residue was purified by column chromatography (EtOAc) to give the title compound as a white solid (0.096 g, 95%). 1H NMR (400 MHz) 8.84 (d, J=0.8 Hz, 2H), 8.34 (d, J=7.6 Hz, 1H), 5.00 (m, 1H), 1.84 (s, 3H), 1.37 (d, J=6.8 Hz, 3H). MS: Calcd.: 183. Found: [M+H]+ 184. Enantiomeric excess determined by HPLC (Chiralpak IA; 95:5 CO2/MeOH), >99% ee.

Workup

  1. additioncharged 150 psi H2
  2. customThe solvent was removed
  3. customthe resulted residue was purified by column chromatography (EtOAc)

Sources & evidence

ORD record
ord-08ff9d3b208c4474a038750b26a2303a
Source dataset
uspto-grants-2014_09
Patent number
US08835465B2

Reaction notes

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