Reacción #218158

Ecuación de reacción

NaBH4

5-(4-formyl-2-methoxyphenoxy)pyrazine-2-carboxamide

amylamine

→

title compound

Rendimiento 71.7%

5-(2-Methoxy-4-pentylaminomethylphenoxy)pyrazine-2-carboxamide

Rendimiento 71.7%

Disolventes

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroDry the column in a vacuum oven at room temperature
2. 2
   OtroPurify
3. 3
   Lavadoby eluting through a 40 g ISCO® column with 60% to 90% (5% (2.0 M NH3 in methanol) in ethyl acetate) in hexanes
4. 4
   ConcentraciónConcentrate the fractions
5. 5
   workup.ADDITIONcontaining the product
6. 6
   Lavadowash with 1.0 N NaOH

Procedimiento

Place 5-(4-formyl-2-methoxyphenoxy)pyrazine-2-carboxamide (Example 719, Part A) (0.200 g, 0.732 mmol), amylamine (0.0670 g, 0.769 mmol) and 3 {acute over (Å)} molecular sieves in a vial. Add methanol (3.6 mL), cap and stir overnight. Add NaBH4 (ca. 3-5 eq in two portions) and stir until the gasses stop evolving. Load the reaction mixture directly onto a 25 g ISCO® pre-load column. Dry the column in a vacuum oven at room temperature. Purify by eluting through a 40 g ISCO® column with 60% to 90% (5% (2.0 M NH3 in methanol) in ethyl acetate) in hexanes. Concentrate the fractions containing the product. Take the solid up in ethyl acetate (50 mL) and wash with 1.0 N NaOH to give the title compound (0.180 g, 71.7%): TOF MS ES+ 345.2 (M+H)+, HRMS calcd for C18H25N4O3 345.1927 (M+H)+, found 345.1926, time 0.52 min; HPLC [Waters XTerra™ C-18 (150×4.6 mm, S-5 microm), 0.1% TFA/acetonitrile in 0.1% TFA/water at 1.0 mL/min, 5-95% over 23 min], tR=10.4 min, 100% purity.

Fuente