Methyl iodide → HCID 67281550, compound

HRID 913033Notes

Reaction equation

HRID 913033 reaction equation
[CH2:1]([O:8][C:9]1[C:14](=[O:15])[C:13]([CH:16]([OH:21])[C:17]([F:20])([F:19])[F:18])=[CH:12][NH:11][C:10]=1[CH3:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23](#N)C.C(=O)([O-])[O-].[K+].[K+].CI>ClCCl>[CH2:1]([O:8][C:9]1[C:14](=[O:15])[C:13]([CH:16]([OH:21])[C:17]([F:20])([F:18])[F:19])=[CH:12][N:11]([CH3:23])[C:10]=1[CH3:22])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 67282369HCID 67282369, compound

Product 1

HCID 67281550HCID 67281550, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-benzyloxy-2-methyl-5-(2,2,2-trifluoro-1-hydroxy-ethyl)-1H-pyridin-4-one (2.07 g, 6.6 mmol), acetonitrile (60 mL), potassium carbonate (2.62 g, 19 mmole) and methyl iodide (15 mL, 0.24 mol) was heated to reflux for 30 min. On cooling to RT, the reaction mixture was filtered over a pad of CELITE™, and the filtrate was concentrated in vacuo to give a solid. The solid was dissolved in dichloromethane, and the resulting solution was washed with brine, dried over Na2SO4, filtered and concentrated to afford 3-benzyloxy-1,2-dimethyl-5-(2,2,2-trifluoro-1-hydroxy-ethyl)-1H-pyridin-4-one (1.48 g. 70% yield, HPLC Method 1 (Example 24), RT=15.4 min, HPLC purity (peak percent area): 99.9% at λ=280 nm). 1H NMR (DMSO-d6+D2O) δ ppm: 7.75 (s, 1H), 7.37, (m, 5H), 5.35 (q, J=7.1 Hz, 1H), 5.01 (m, 2H), 3.63 (s, 3H), 2.18 (s, 3H); MS-ESI (m/z) 328.1 [M+1]+, 220.2, 91.2 (100%).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 30 min
  3. filtrationthe reaction mixture was filtered over a pad of CELITE™
  4. concentrationthe filtrate was concentrated in vacuo
  5. customto give a solid
  6. washthe resulting solution was washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-99dd5e3992854bfdb013e0c45f78f42a
Source dataset
uspto-grants-2011_09
Patent number
US08026261B2

Reaction notes

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