Reaktion #66684

Reaktionsgleichung

5-(2,4-Diamino-pyrimidin-5-yloxy)-4-isopropyl-2-methoxy-thiobenzamide

HOAc

NaHCO3

→

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

Ausbeute 28.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   ExtraktionThe aqueous solution was extracted into methylene chloride
2. 2
   ExtraktionThe combined organic extract
3. 3
   Trocknenwas dried over Na2SO4
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated

Vorschrift

To a solution of 5-(2,4-Diamino-pyrimidin-5-yloxy)-4-isopropyl-2-methoxy-thiobenzamide (0.23 g, 0.69 mmol) in HOAc (5 ml) was added bromoactaldehyde diethylacetal (0.18 g, 0.9 mmol) and TsOH (5 mg) as a catalyst. The reaction mixture was heated at 110° C. for 16 hrs and basified with sat. NaHCO3 solution. The aqueous solution was extracted into methylene chloride. The combined organic extract was dried over Na2SO4, filtered and concentrated. Flash chromatography on silica (5% MeOH in methylene chloride with 1% NH4OH) gave 5-(2-Isopropyl-4-methoxy-5-thiazol-2-yl-phenoxy)-pyrimidine-2,4-diamine (0.070 g, 28%) as a yellow solid. (M+H)=358.

Quelle