Methyl iodide → 4-(5-Bromothiophen-2-yl)-2-methylsulfanylpyrimidine

HRID 1716385Notes

Reaction equation

HRID 1716385 reaction equation
[Br:1][C:2]1[S:6][C:5]([C:7]2[CH:12]=[CH:11][N:10]=[C:9]([SH:13])[N:8]=2)=[CH:4][CH:3]=1.[CH3:14]I>O.[OH-].[Na+].CCO>[Br:1][C:2]1[S:6][C:5]([C:7]2[CH:12]=[CH:11][N:10]=[C:9]([S:13][CH3:14])[N:8]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 6328Methyl iodideHCID 178527860HCID 178527860, compound

Product 1

HCID 28205344-(5-Bromothiophen-2-yl)-2-methylsulfanylpyrimidineYield 88.6%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

4-(5-Bromothiophen-2-yl)-pyrimidine thiol (2.5 g, 9.15 mmol) was completely dissolved in 14.8 mL DI water and 2.4 mL 4 N NaOH. The mixture was diluted with EtOH (25 mL) and MeI (0.598 mL, 9.61 mmol) was added. The reaction was stirred 18 hours. The yellow solids were collected by filtration, washed with EtOH and dried to afford 4-(5-Bromothiophen-2-yl)-2-methylsulfanyl-pyrimidine (2.32 g, 88.6%) as a pale yellow solid. MS: m/z 287 (M+H+).

Workup

  1. additionwas added
  2. filtrationThe yellow solids were collected by filtration
  3. washwashed with EtOH
  4. customdried

Sources & evidence

ORD record
ord-72a7db485f6342fa8c41bb88a3caf18d
Source dataset
uspto-grants-2010_09
Patent number
US07803806B2

Reaction notes

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