Methyl iodide → HCID 67299926, compound

HRID 1260299Notes

Reaction equation

HRID 1260299 reaction equation
[Br:1][C:2]1[C:3]([C:11]([OH:13])=[O:12])=[N:4][C:5]([CH2:8][O:9][CH3:10])=[N:6][CH:7]=1.[C:14]([O-])([O-])=O.[Cs+].[Cs+].CI>CC(C)=O>[CH3:14][O:12][C:11]([C:3]1[C:2]([Br:1])=[CH:7][N:6]=[C:5]([CH2:8][O:9][CH3:10])[N:4]=1)=[O:13]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 67299931HCID 67299931, compound

Product 1

HCID 67299926HCID 67299926, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 5-bromo-2-methoxymethyl-pyrimidine-4-carboxylic acid (2.5 g, 10.1 mmol) in acetone (100 ml) was added Cs2CO3 (19.8 g, 60.7 mmol) followed by methyliodide (3.8 ml, 60.7 mmol). The mixture was heated to reflux for 8 h. The reaction mixture was then filtered, and the filtrate was evaporated. The crude material was purified by silica gel chromatography using a ethyl acetate/hexane eluent to yield 700 mg (27%) of the title compound as yellow oil.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 8 h
  3. filtrationThe reaction mixture was then filtered
  4. customthe filtrate was evaporated
  5. customThe crude material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-c78530ccd1294539a1ce4c5147b390f8
Source dataset
uspto-grants-2013_06
Patent number
US08470820B2

Reaction notes

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