반응 #1017092

반응 방정식

2-chloro-N-(2,6-dichlorobenzyl)pyrimidin-4-amine

(S)-2-(4-amino-1H-pyrazol-1-yl)-N-(1-hydroxypropan-2-yl)acetamide

Xantphos

cesium carbonate

→

(S)-2-(4-((4-((2,6-dichlorobenzyl)amino)pyrimidin-2-yl)amino)-1H-pyrazol-1-yl)-N-(1-hydroxypropan-2-yl)acetamide

용매

dioxane

반응 조건

후처리

1. 1
   온도was heated
2. 2
   온도to reflux under nitrogen
3. 3
   농축Upon completion, the reaction was concentrated in vacuo
4. 4
   workup.ADDITIONdiluted with aqueous sodium carbonate solution
5. 5
   추출then extracted with ethyl acetate
6. 6
   건조The organic layer was dried (Na2SO4)
7. 7
   농축concentrated in vacuo
8. 8
   기타purified by column chromatography (0-10% v/v [10% NH3 in MeOH]/DCM)

실험 절차

A mixture of 2-chloro-N-(2,6-dichlorobenzyl)pyrimidin-4-amine (120 mg, 0.41 mmol), (S)-2-(4-amino-1H-pyrazol-1-yl)-N-(1-hydroxypropan-2-yl)acetamide V-1 (110 mg, 0.54 mmol, prepared by Procedure G1), Xantphos (47 mg, 0.08 mmol), Pd2dba3 (37 mg, 0.04 mmol) and cesium carbonate (333 mg, 1.02 mmol) in dioxane (40 mL) was heated to reflux under nitrogen. Upon completion, the reaction was concentrated in vacuo, diluted with aqueous sodium carbonate solution then extracted with ethyl acetate. The organic layer was dried (Na2SO4), concentrated in vacuo and purified by column chromatography (0-10% v/v [10% NH3 in MeOH]/DCM) to afford (S)-2-(4-((4-((2,6-dichlorobenzyl)amino)pyrimidin-2-yl)amino)-1H-pyrazol-1-yl)-N-(1-hydroxypropan-2-yl)acetamide I-3 (60 mg, 25%). LC-MS (Method A), RT=8.32 min. (ES+) 450.

출처