Methyl iodide → HCID 58128708, compound

HRID 2088446Notes

Reaction equation

HRID 2088446 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[NH:8][C:9](=[O:13])[N:10]([CH3:12])[CH:11]=1)=[O:5])[CH3:2].[CH3:21][Si](C)(C)N[Si](C)(C)C.[K].CI>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[CH:7]([C:14]2[CH:15]=[CH:16][C:17]([F:20])=[CH:18][CH:19]=2)[N:8]([CH3:21])[C:9](=[O:13])[N:10]([CH3:12])[CH:11]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 45051783Silanamine, 1,1,1-trimethyl-N-(trimethylsilyl)-, potassium saltHCID 58128634HCID 58128634, compound

Product 1

HCID 58128708HCID 58128708, compoundYield 66.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(4-Fluoro-phenyl)-1-methyl-2-oxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid ethyl ester (1.0 g, 3.6 mmol) was dissolved in 10 mL DMF and cooled to 0°. Potassium hexamethyldisilazane (8 mL, 4 mmol of 0.5M toluene solution) was added and the reaction mixture was stirred at 0° for 5 minutes. CH3I (0.3 mL, 4.8 mmol) was added and the mixture was allowed to warm to room temperature and stir for 2 hours. The solution was poured into cold aqueous pH 2 buffer and extracted with ethyl acetate. The organic layer was dried over Na2SO4, filtered and the solvent removed in vacuo. The residue was chromatographed in 0-30% ethyl acetate/hexane to yield 700 mg of 4-(4-fluoro-phenyl)-1,3-dimethyl-2-oxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid ethyl ester.

Workup

  1. temperaturecooled to 0°
  2. stirringstir for 2 hours
  3. additionThe solution was poured into cold aqueous pH 2 buffer
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. customthe solvent removed in vacuo
  8. customThe residue was chromatographed in 0-30% ethyl acetate/hexane

Sources & evidence

ORD record
ord-209c71cf0df44c8dbe61f9b51c69035c
Source dataset
uspto-grants-2013_05
Patent number
US08435990B2

Reaction notes

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