Methyl iodide → HCID 58298344, compound

HRID 425244Notes

Reaction equation

HRID 425244 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9]2[CH:10]=[C:11]([C:20]#[N:21])[N:12]3[C:17]([SH:18])=[CH:16][C:15]([CH3:19])=[N:14][C:13]=23)=[C:4]([CH3:22])[CH:3]=1.[CH3:23]I>[OH-].[Na+]>[Br:1][C:2]1[CH:3]=[C:4]([CH3:22])[C:5]([C:9]2[CH:10]=[C:11]([C:20]#[N:21])[N:12]3[C:17]([S:18][CH3:23])=[CH:16][C:15]([CH3:19])=[N:14][C:13]=23)=[C:6]([CH3:8])[CH:7]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 178429705HCID 178429705, compound

Product 1

HCID 58298344HCID 58298344, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 8-(4-bromo-2,6-dimethyl-phenyl)-4-mercapto-2-methyl-pyrrolo[1,2-a]pyrimidine-6-carbonitrile (7.50 g), MeI (12.5 mL) in 1 M NaOH aqueous solution (100 mL) was stirred at room temperature for 1 h. The reaction mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to give crude 8-(4-bromo-2,6-dimethyl-phenyl)-2-methyl-4-methylsulfanyl-pyrrolo[1,2-a]pyrimidine-6-carbonitrile (5.75 g). This product was used in the next step without further purification.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-045b4e8950fe43939e1dcbcd9e43426b
Source dataset
uspto-grants-2012_01
Patent number
US08106194B2

Reaction notes

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