تفاعل #610186

معادلة التفاعل

2-bromo-N-tert-butyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

1,3-dimethyl-1H-pyrazol-4-amine

xantphos

cesium carbonate

→

N-tert-butyl-2-(1,3-dimethyl-1H-pyrazol-4-ylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

المردود 55.3%

المذيبات

dioxane

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe mixture was cooled
2. 2
   ترشيحthen filtered through a pad of celite
3. 3
   تركيزThe filtrate was concentrated in vacuo
4. 4
   أخرىthen purified by chromatography (silica, 25-100% ethyl acetate in hexanes) lo

الإجراء التجريبي

A mixture of 2-bromo-N-tert-butyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (150 mg, 351 μmol), 1,3-dimethyl-1H-pyrazol-4-amine (58.5 mg, 526 μmol), xantphos (60.9 mg, 105 μmol), Pd2(dba)3 (32.1 mg, 35.1 μmol) and cesium carbonate (229 mg, 702 μmol) in dioxane (2 mL) was heated in a microwave at 150° C. for 20 min. The mixture was cooled then filtered through a pad of celite. The filtrate was concentrated in vacuo then purified by chromatography (silica, 25-100% ethyl acetate in hexanes) lo give N-tert-butyl-2-(1,3-dimethyl-1H-pyrazol-4-ylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (89 mg, 194 μmol, 55%) as a yellow gum. (EI/CI) m/z: 458.3 [M+H].

المصدر