Methyl iodide → HCID 58166486, compound

HRID 1405972Notes

Reaction equation

HRID 1405972 reaction equation
[F:1][C:2]1[C:3]([NH:9][C:10](=[O:18])[C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)=[N:4][C:5]([OH:8])=[N:6][CH:7]=1.[C:19]([O-])([O-])=O.[K+].[K+].IC>CN(C=O)C>[F:1][C:2]1[C:3]([NH:9][C:10](=[O:18])[C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)=[N:4][C:5](=[O:8])[N:6]([CH3:19])[CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178425850HCID 178425850, compound

Product 1

HCID 58166486HCID 58166486, compoundYield 8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To N-(5-fluoro-2-hydroxypyrimidin-4-yl)-4-methylbenzamide (200 mg, 0.81 mmol) in DMF (5 mL) was added K2CO3 (224 mg, 1.6 mmol), and iodomethane (230 mg, 1.6 mmol). The mixture was stirred and heated to 60° C. for 30 min and then stirred for 16 h at room temperature. The mixture was partitioned between ethyl acetate (EtOAc) and water (H2O). The organic phase was dried over magnesium sulfate (MgSO4), filtered and evaporated. The crude material was purified by reverse phase chromatography to yield the title compound as a white solid (17 mg, 8%): mp 229-230° C.; 1H NMR (300 MHz, CDCl3) δ13.2 (br s, 1H), 8.23-8.15 (br m, 2H), 7.42-7.37 (br m, 1H), 7.30-7.25 (br m, 2H), 3.45 (s, 3H), 2.44 (s, 3H); ESIMS m/z 262 ([M+H]+), m/z 260 ([M−H]−).

Workup

  1. stirringstirred for 16 h at room temperature
  2. customThe mixture was partitioned between ethyl acetate (EtOAc) and water (H2O)
  3. dry with materialThe organic phase was dried over magnesium sulfate (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude material was purified by reverse phase chromatography

Sources & evidence

ORD record
ord-48978aa15dac4f93aa841e6cea05a52e
Source dataset
uspto-grants-2014_12
Patent number
US08916579B2

Reaction notes

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