Methyl iodide → HCID 89579960, compound

HRID 2276810Notes

Reaction equation

HRID 2276810 reaction equation
[C:1]([C:3]1[CH:26]=[CH:25][C:6]([O:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]3[N:19]=[C:18]([C:20]([OH:22])=[O:21])[CH:17]=[C:16]([CH:23]=[CH2:24])[N:15]=3)=[CH:10][CH:9]=2)=[CH:5][C:4]=1[C:27]([F:30])([F:29])[F:28])#[N:2].[C:31](=O)([O-])[O-].[K+].[K+].IC>CN(C=O)C.O>[C:1]([C:3]1[CH:26]=[CH:25][C:6]([O:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]3[N:19]=[C:18]([C:20]([O:22][CH3:31])=[O:21])[CH:17]=[C:16]([CH:23]=[CH2:24])[N:15]=3)=[CH:10][CH:9]=2)=[CH:5][C:4]=1[C:27]([F:30])([F:29])[F:28])#[N:2]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 89579710HCID 89579710, compound

Product 1

HCID 89579960HCID 89579960, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

In a 50-mL vial with a screw-top septum 2-(4-(4-cyano-3-(trifluoromethyl) phenoxy)phenyl)-6-vinylpyrimidine-4-carboxylic acid (340 mg, 0.83 mmol) was dissolved in DMF (5 mL) and treated with potassium carbonate (343.6 mg, 2.49 mmol) and iodomethane (0.5 mL). The mixture was stirred at room temperature for three hours, diluted with 100 mL water, and extracted with 2×50 mL diethyl ether. The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure to provide methyl 2-(4-(4-cyano-3-(trifluoromethyl) phenoxy)phenyl)-6-vinylpyrimidine-4-carboxylate. The residue was used in the next step without purification. LC/MS: m/z=426 [M+H]+.

Workup

  1. extractionextracted with 2×50 mL diethyl ether
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-65977751e830494b9ad6a650d74b5fa9
Source dataset
uspto-grants-2015_09
Patent number
US09133131B2

Reaction notes

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