Methyl iodide → Ethyl 4-(2-chloro-4-fluorophenyl)-1,6-dimethyl-2-(thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylate

HRID 524620Notes

Reaction equation

HRID 524620 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:13]([CH3:20])[NH:12][C:11]([C:21]2[S:22][CH:23]=[CH:24][N:25]=2)=[N:10]1.IC.[C:28](=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:13]([CH3:20])[N:12]([CH3:28])[C:11]([C:21]2[S:22][CH:23]=[CH:24][N:25]=2)=[N:10]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 490024Ethyl 4-(2-chloro-4-fluoro-phenyl)-6-methyl-2-thiazol-2-yl-1,4-dihydropyrimidine-5-carboxylate

Product 1

HCID 90042905Ethyl 4-(2-chloro-4-fluorophenyl)-1,6-dimethyl-2-(thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylateYield 48%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of ethyl 4-(2-chloro-4-fluorophenyl)-6-methyl-2-(thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylate (2 g, 5.3 mmol), iodomethane (0.97 g, 6.84 mmol) and potassium carbonate (1.47 g, 10.6 mmol) in acetonitrile (50 mL) was stirred at 70° C. for 12 hours, and cooled to 25° C. The reaction mixture was filtered and the filtrate was concentrated in vacuo. The residue was purified by a silica gel column chromatography (PETROLEUM ETHER/EtOAc (V/V)=3/1) to give the title compound as a tawny solid (1.0 g, 48%). The compound was characterized by the following spectroscopic data:

Workup

  1. temperaturecooled to 25° C
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was purified by a silica gel column chromatography (PETROLEUM ETHER/EtOAc (V/V)=3/1)

Sources & evidence

ORD record
ord-f35b735884de4535b6f60f93e56fd9d5
Source dataset
uspto-grants-2016_05
Patent number
US09340538B2

Reaction notes

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