Reacción #63032

Ecuación de reacción

XIII

1-(2-cyanoethylamino)-5-(4,6-dimethyl-2-pyrimidylamino)pentane

tetradecanoyl chloride

→

crude product

1-[N-(2-cyanoethyl)tetradecanamido]-5-(4,6-dimethyl-2-pyrimidylamino)-pentane

Disolventes

pyridine

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added
2. 2
   workup.ADDITIONwas added
3. 3
   Otrothe reaction to completion
4. 4
   workup.ADDITIONIce was then added
5. 5
   Otroto quench the reaction
6. 6
   workup.ADDITIONfollowed by the addition of CHCl3
7. 7
   ExtracciónThe mixture was first extracted with 10% NaHCO3
8. 8
   Otrowith 1M HOAc to remove the bulk of the pyridine
9. 9
   OtroThe remaining CHCl3 phase was evaporated

Procedimiento

Crude XIII was dissolved in dry pyridine to which 1 eq of tetradecanoyl chloride was added with stirring. The run was followed by tlc and excess acid chloride was added to drive the reaction to completion. Ice was then added to quench the reaction followed by the addition of CHCl3. The mixture was first extracted with 10% NaHCO3 and then with 1M HOAc to remove the bulk of the pyridine. The remaining CHCl3 phase was evaporated to yield the crude product which was purified by chromatography on a 100 g silica gel (Brinkman 50-200μ) column developed with 30% acetone/chloroform. The product (1 g) was collected after only 150 ml of eluant had passed through the column and was only partially purified.

Fuente