Réaction #66668

Équation de réaction

potassium acetate

thiazole

5-(5-Iodo-2-isopropyl-4-methoxy-phenoxy)-pyrimidine-2,4-diamine

5-(5-iodo-2-isopropyl-4-methoxy-phenoxy)-pyrimidine-2,4-diamine

→

5-(2-isopropyl-4-methoxy-5-thiazol-5-yl-phenoxy)-pyrimidine-2,4-diamine

Rendement 9.1%

Solvants

N,N-dimethylacetamide

Conditions de réaction

Traitement

1. 1
   AutreThe cooled reaction
2. 2
   Extractionwas extracted with dichloromethane (100 mL) and water (2×100 mL)
3. 3
   SéchageThe dichloromethane layer was dried
4. 4
   Concentrationconcentrated
5. 5
   Autrepurified by silica gel column chromatography
6. 6
   Lavageeluting with 95/5/0.1 dichloromethane/methanol/ammonium hydroxide

Mode opératoire

To 5-(5-Iodo-2-isopropyl-4-methoxy-phenoxy)-pyrimidine-2,4-diamine (600 mg, 1.5 mmol, from Example 14, Step 1) dissolved in N,N-dimethylacetamide (4.8 mL) was added potassium acetate (221 mg, 2.24 mmol), thiazole (0.53 mL, 7.5 mmol) and tetrakis(triphenylphosphine)palladium(0) (70 mg, 0.06 mmol). After heating at 115° C. overnight. The cooled reaction was extracted with dichloromethane (100 mL) and water (2×100 mL). The dichloromethane layer was dried using anhydrous sodium sulfate, concentrated and purified by silica gel column chromatography eluting with 95/5/0.1 dichloromethane/methanol/ammonium hydroxide to yield 5-(2-isopropyl-4-methoxy-5-thiazol-5-yl-phenoxy)-pyrimidine-2,4-diamine (49 mg, 9%) as pale yellow solid, MS (M+H)=358.

Source