Sodium Bicarbonate → 5-(Methylthio)pyrazin-2-amine

HRID 1814132Notes

Reaction equation

HRID 1814132 reaction equation
[NH2:1][C:2]1[CH:7]=[N:6][C:5](Br)=[CH:4][N:3]=1.[Na].[CH3:10][SH:11].C(=O)([O-])O.[Na+]>CN(C)C=O>[NH2:1][C:2]1[CH:7]=[N:6][C:5]([S:11][CH3:10])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 5995392-Amino-5-bromopyrazineHCID 45051789Methylmercaptan sodium

Product 1

HCID 218972225-(Methylthio)pyrazin-2-amineYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of 2-amino-5-bromopyrazine (100 mg), 95% methanethiol sodium salt (84.8 mg) and tetrakistriphenylphosphine palladium (66.4 mg) in N,N-dimethylformamide (2.9 ml) was stirred at 60° C. for 15 hours. After completion of the reaction, the reaction solution was poured into a saturated aqueous sodium hydrogencarbonate solution, extracted with toluene, washed with a saturated aqueous NaCl solution, dried over anhydrous sodium sulfate, filtered and concentrated. The resulting residue was separated using silica gel column chromatography (ethyl acetate:hexane=1:2) to obtain 67.8 mg (84%) of the desired product as a white powder.

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with toluene
  3. washwashed with a saturated aqueous NaCl solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting residue was separated

Sources & evidence

ORD record
ord-24b5b2e483eb400491bd7d0929f48994
Source dataset
uspto-grants-2005_04
Patent number
US06875770B2

Reaction notes

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