Trifluoroacetic acid → Ammonium Hydroxide

HRID 719923Notes

Reaction equation

HRID 719923 reaction equation
C([O:5]C(=O)[NH:7][C:8]1[CH:13]=[N:12][C:11]([CH2:14][C:15]#[N:16])=[CH:10][N:9]=1)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[OH-:5].[NH4+:7].[NH2:7][C:8]1[N:9]=[CH:10][C:11]([CH2:14][C:15]#[N:16])=[N:12][CH:13]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67482585Tert-butyl 5-(cyanomethyl)pyrazin-2-ylcarbamate

Product 2

HCID 14923Ammonium HydroxideYield 0.1%HCID 21897307HCID 21897307, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

A solution of (5-cyanomethyl-pyrazin-2-yl)-carbamic acid tert-butyl ester (807.6 mg, 3.447 mol) in methylene chloride (4.3 mL) was treated with trifluoroacetic acid (2.7 mL, 34.470 mmol). The reaction mixture was stirred at 25° C. for 2 h and then concentrated in vacuo. Biotage chromatography (FLASH 40S, Silica, 1/9 methanol/methylene chloride with 0.1% ammonium hydroxide) afforded impure (5-amino-pyrazin-2-yl)-acetonitrile. Re-purification by Biotage chromatography (FLASH 40M, Silica, 99/1 ethyl acetate/methanol) afforded pure (5-amino-pyrazin-2-yl)-acetonitrile (281.4 mg, 60.8%) as an orange solid: mp 132–134° C.; EI-HRMS m/e calcd for C6H6N4 (M+) 134.0592, found 134.0593.

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-23da45ecd93d4028af9b9ccaa721050c
Source dataset
uspto-grants-2006_11
Patent number
US07132425B2

Reaction notes

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