Trifluoroacetic acid → 5-Methylsulfanylmethyl-pyrazin-2-ylamine

HRID 719920Notes

Reaction equation

HRID 719920 reaction equation
C([O:5]C(=O)[NH:7][C:8]1[CH:13]=[N:12][C:11]([CH2:14][S:15][CH3:16])=[CH:10][N:9]=1)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[OH-:5].[NH4+:7].[CH3:16][S:15][CH2:14][C:11]1[N:12]=[CH:13][C:8]([NH2:7])=[N:9][CH:10]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 67482522(5-Methylsulfanylmethyl-pyrazin-2-yl)-carbamic acid tert-butyl ester

Product 2

HCID 14923Ammonium HydroxideYield 0.1%HCID 218973395-Methylsulfanylmethyl-pyrazin-2-ylamineYield 201.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

A solution of (5-methylsulfanylmethyl-pyrazin-2-yl)-carbamic acid tert-butyl ester (0.45 g, 1.762 mmol) in methylene chloride (18 mL) was treated with trifluoroacetic acid (1.4 mL, 18.172 mmol) and then was stirred at 25° C. for 2 h 15 min. The reaction solution was then treated with a second aliquot of trifluoroacetic acid (0.7 mL, 9.086 mmol) and was stirred at 25° C. for 5 h. At this time, the reaction mixture was concentrated in vacuo. Biotage chromatography (FLASH 40S, Silica, 1/9 methanol/methylene chloride with 0.1% ammonium hydroxide) afforded 5-methylsulfanylmethyl-pyrazin-2-ylamine (276.1 mg, quant.) as a white solid: mp 102.0–102.7° C.; EI-HRMS m/e calcd for C6H9N3S (M+) 155.0517, found 155.0516.

Workup

  1. stirringwas stirred at 25° C. for 5 h
  2. concentrationAt this time, the reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-4e9e437dc3bf4b389f8d3d4843900b0f
Source dataset
uspto-grants-2006_11
Patent number
US07132425B2

Reaction notes

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