Reaktion #528155

Reaktionsgleichung

2,4-diamino-6-ethyl-5-(4-chloro-3-decylcarbonylaminophenyl)pyrimidine

hydrochloric acid

sodium hydroxide

→

2,4-diamino-6-ethyl-5-(4-chloro-3-undecylaminophenyl)pyrimidine

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturUnder a nitrogen atmosphere, a stirred solution of 40 mL of 1M borane-tetrahydrofuran complex was cooled to below 10° C.
2. 2
   TemperaturThe reaction mixture temperature was maintained below 10° C. throughout the addition
3. 3
   workup.ADDITIONUpon completion of addition
4. 4
   Temperaturto cool to ambient temperature
5. 5
   Extraktionit was extracted with two 150 mL portions of ethyl acetate
6. 6
   TrocknenThe combined extracts were dried with magnesium sulfate
7. 7
   Filtrationfiltered
8. 8
   EinengenThe filtrate was concentrated under reduced pressure to a residue
9. 9
   WaschenElution
10. 10
    Einengenconcentrated under reduced pressure
11. 11
    Sonstigeyielding when
12. 12
    Sonstigedried

Vorschrift

Under a nitrogen atmosphere, a stirred solution of 40 mL of 1M borane-tetrahydrofuran complex was cooled to below 10° C., and a solution of 2.4 grams (0.006 mole) of 2,4-diamino-6-ethyl-5-(4-chloro-3-decylcarbonylaminophenyl)pyrimidine in 60 mL of tetrahydrofuran was added dropwise during about a 5 minute period. The reaction mixture temperature was maintained below 10° C. throughout the addition. Upon completion of addition, the reaction mixture was heated at 60° C. for about 18 hours. After this time, the reaction mixture was allowed to cool to ambient temperature, where it was stirred for about 24 hours. The reaction mixture was then made acidic with aqueous 2N hydrochloric acid, after which time it was stirred for about 15 minutes. The mixture was made basic with aqueous 10% sodium hydroxide, and then it was extracted with two 150 mL portions of ethyl acetate. The combined extracts were dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residue. The residue was subjected to column chromatography on silica gel. Elution was accomplished using 10:1 methylene chloride and methanol. The product-containing fractions were combined and concentrated under reduced pressure, yielding when dried, 0.7 gram of 2,4-diamino-6-ethyl-5-(4-chloro-3 -undecylaminophenyl)pyrimidine. The NMR spectrum was consistent with the proposed structure.

Quelle