Sodium Cyanide → Tert-butyl 5-(cyanomethyl)pyrazin-2-ylcarbamate

HRID 719922Notes

Reaction equation

HRID 719922 reaction equation
[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[CH:13]=[N:12][C:11]([CH2:14]Br)=[CH:10][N:9]=1)([CH3:4])([CH3:3])[CH3:2].[C-:17]#[N:18].[Na+]>CN(C)C=O.[Cl-].[Na+]>[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[CH:13]=[N:12][C:11]([CH2:14][C:17]#[N:18])=[CH:10][N:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 45073740tert-Butyl (5-(bromomethyl)pyrazin-2-yl)carbamate

Product 1

HCID 67482585Tert-butyl 5-(cyanomethyl)pyrazin-2-ylcarbamateYield 99.4%

Reagents, catalysts & solvents 2

HCID 5234Sodium ChlorideSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

A solution of (5-bromomethyl-pyrazin-2-yl)-carbamic acid tert-butyl ester (prepared according to WO 02/070494, 1.00 g, 3.470 mmol) in N,N-dimethylformamide (6.9 mL) was treated with sodium cyanide (350.7 mg, 6.940 mmol). The reaction mixture was stirred at 40° C. for 1 h. The reaction was diluted with a saturated aqueous sodium chloride solution (100 mL) and then extracted with ethyl acetate (100 mL). The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 40L, Silica, 3/7 ethyl acetate/hexanes) afforded (5-cyanomethyl-pyrazin-2-yl)-carbamic acid tert-butyl ester (807.6 mg, 99%) as a light yellow solid: mp 162–164° C.; EI-HRMS m/e calcd for C11H14N4O2 (M+) 234.1117, found 234.1120.

Workup

  1. extractionextracted with ethyl acetate (100 mL)
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8cfb553cee624a258b17edfdda04b09f
Source dataset
uspto-grants-2006_11
Patent number
US07132425B2

Reaction notes

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