Methyl iodide → 2-(1-Methyl-4-phenyl-1H-imidazol-5-yl)-7-(methylthio)[1,3]thiazolo[5,4-d]pyrimidine

HRID 32548Notes

Reaction equation

HRID 32548 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[S:8][C:9]3[N:10]=[CH:11][N:12]=[C:13]([SH:16])[C:14]=3[N:15]=2)=[C:5]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:4]=[CH:3]1.[CH3:23]I>[OH-].[Na+]>[CH3:1][N:2]1[C:6]([C:7]2[S:8][C:9]3[N:10]=[CH:11][N:12]=[C:13]([S:16][CH3:23])[C:14]=3[N:15]=2)=[C:5]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:4]=[CH:3]1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 178481247HCID 178481247, compound

Product 1

HCID 691944652-(1-Methyl-4-phenyl-1H-imidazol-5-yl)-7-(methylthio)[1,3]thiazolo[5,4-d]pyrimidineYield 95%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

2-(1-Methyl-4-phenyl-1H-imidazol-5-yl)[1,3]thiazolo[5,4-d]pyrimidine-7-thiol (Example 31) (2.91 g) was dissolved in 2M NaOH (50 mL) then methyl iodide (0.67 mL) added under an inert atmosphere at ambient temperature. After 2.5 hours the reaction mixture was filtered, washed with water, dried under high-vacuum to give the title compound as a pale brown solid (2.9 g, 95%);

Workup

  1. filtrationAfter 2.5 hours the reaction mixture was filtered
  2. washwashed with water
  3. customdried under high-vacuum

Sources & evidence

ORD record
ord-52177757f59b430a9c165956debd55c0
Source dataset
uspto-grants-2008_09
Patent number
US07427616B2

Reaction notes

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