Sodium methanethiolate → 6-Bromo-8-(methylthio)imidazo[1,2-A]pyrazine

HRID 1498613Notes

Reaction equation

HRID 1498613 reaction equation
[Br:1][C:2]1[N:3]=[C:4](Br)[C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[CH:7]=1.[CH3:12][S-:13].[Na+]>CO.O>[Br:1][C:2]1[N:3]=[C:4]([S:13][CH3:12])[C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[CH:7]=1

Participants

5

Reactant 2

HCID 4378561Sodium methanethiolateHCID 150258436,8-Dibromoimidazo[1,2-a]pyrazine

Product 1

HCID 532498696-Bromo-8-(methylthio)imidazo[1,2-A]pyrazineYield 70%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a stirred suspension of 489 g (1766 mmol) 6,8-dibromo-imidazo[1,2-a]pyrazine which was prepared according to a procedure described in the Journal of Medicinal Chemistry, 1984, vol. 27, #2, p. 206-212 in 2.9 L methanol at −20° C. was dropwise added a solution of 225 g sodium methanethiolate in 800 mL water. After stirring overnight, the clear solution was poured into 30 L water, the precipitate was filtered, washed with water and dried in vaccuo to yield 301 g (70%) of the title compound.

Workup

  1. customwas prepared
  2. filtrationthe precipitate was filtered
  3. washwashed with water
  4. customdried in vaccuo

Sources & evidence

ORD record
ord-f0be9e5ab2d841588530516a7f934f89
Source dataset
uspto-grants-2015_12
Patent number
US09199999B2

Reaction notes

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