تفاعل #1330165

معادلة التفاعل

N,N′-Dimethylethylenediamine

cyclohexanecarboxamide

5-bromopyrimidine

K3PO4

→

title compound

المردود 75.0%

Cyclohexanecarboxylic acid pyrimidin-5-yl-amide

المردود 75.0%

المذيبات

dioxane

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONAn oven-dried resealable Schlenk tube containing a stirbar
2. 2
   أخرىevacuated
3. 3
   أخرىscrew cap
4. 4
   أخرىThe tube was sealed
5. 5
   أخرىThe contents of the tube were then partitioned between water and dichloromethane
6. 6
   أخرىThe aqueous layer was separated
7. 7
   استخلاصextracted two times with additional dichloromethane
8. 8
   تجفيفdried over Na2SO4
9. 9
   ترشيحfiltered
10. 10
    تركيزconcentrated under reduced pressure
11. 11
    أخرىThe residue was chromatographed on silica gel
12. 12
    أخرىfollowed by recrystallization from dichloromethane/hexane

الإجراء التجريبي

An oven-dried resealable Schlenk tube containing a stirbar was charged with CuI (20 mg, 0.1 mmol, 10 mol %), cyclohexanecarboxamide (153 mg, 1.2 mmol), 5-bromopyrimidine (160 mg, 1 mmol), and K3PO4 (425 mg, 2 mmol), evacuated and backfilled with argon. N,N′-Dimethylethylenediamine (8.9 mg, 0.1 mmol) and dioxane (1 ml) were injected, and under a flow of argon, the septum was replaced by a Teflon screw cap. The tube was sealed, and the mixture was stirred and heated in an oil bath at 110° C. for 16 h. The contents of the tube were then partitioned between water and dichloromethane. The aqueous layer was separated, and extracted two times with additional dichloromethane. The organics were then combined, dried over Na2SO4, filtered, concentrated under reduced pressure. The residue was chromatographed on silica gel followed by recrystallization from dichloromethane/hexane to give 154 mg (75%) of the title compound as a solid. 1H NMR (CDCl3, 300 MHz): δ 9.02 (s, 2H), 8.97 (s, 1H), 7.40 (br s, 1H), 2.32 (tt, 1H, J=3.6, 11.4 Hz), 2.10–1.20 (m, 10H).

المصدر