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

HRID 1012171Notes

Reaction equation

HRID 1012171 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-ccd8df26c63b430a937d6e6a4b24f711
Source dataset
uspto-grants-2011_07
Patent number
US07977481B2

Reaction notes

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