Methyl iodide → HCID 59580515, compound

HRID 2199204Notes

Reaction equation

HRID 2199204 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[S:9][C:10]([N:13]([CH3:21])[C:14]([NH:16][CH2:17][CH2:18][S:19][CH3:20])=[O:15])=[CH:11][N:12]=2)[CH:5]=[N:6][CH:7]=1.[H-].[Na+].I[CH3:25]>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[S:9][C:10]([N:13]([CH3:21])[C:14]([N:16]([CH3:25])[CH2:17][CH2:18][S:19][CH3:20])=[O:15])=[CH:11][N:12]=2)[CH:5]=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 59580437HCID 59580437, compound

Product 1

HCID 59580515HCID 59580515, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of [2-(5-fluoropyridin-3-yl)-thiazol-5-yl]-1-methyl-3-(2-methylsulfanyl-ethyl)urea (173 mg, 0.53 mmol) in DMF (5 mL) cooled to 0° C. was added NaH (26 mg, 0.65 mmol, 60% dispersion in mineral oil) and the mixture was stirred for 30 min. To this was added iodomethane (47 μL, 0.75 mmol) and the reaction mixture was stirred for 1 h. The reaction was quenched by addition of ethyl acetate and 1 N HCl. The layers were separated, and the ethyl acetate layer was washed three times with water and once with brine, dried over MgSO4, filtered and concentrated to dryness under reduced pressure to give the desired product as a yellow solid (0.110 g, 61%): mp 68-69° C.; 1H NMR (300 MHz, CDCl3) δ 8.90 (s, 1H), 8.47 (d, J=2.8 Hz, 1H), 7.93 (dt, J=9.3, 2.2 Hz, 1H), 7.45 (s, 1H), 3.54 (t, J=6.9 Hz, 2H), 3.41 (s, 3H), 2.94 (s, 3H), 2.74 (t, J=7.1 Hz, 2H), 2.16 (s, 3H); ESIMS m/z 341.1 (M+1).

Workup

  1. stirringthe reaction mixture was stirred for 1 h
  2. customThe reaction was quenched by addition of ethyl acetate and 1 N HCl
  3. customThe layers were separated
  4. washthe ethyl acetate layer was washed three times with water
  5. dry with materialonce with brine, dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-0985c315fa5f44a6809520306f2f5bf8
Source dataset
uspto-grants-2016_06
Patent number
US09357780B2

Reaction notes

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