Reaktion #2189560

Reaktionsgleichung

4-chloro-5-(1,3-thiazol-2-yl)thieno[2,3-d]pyrimidine

5-(3-aminopropoxy)-N-methylpyridine-2-carboxamide trifluoroacetate

potassium carbonate

→

N-methyl-5-(3-[5-(1,3-thiazol-2-yl)thieno[2,3-d]pyrimidin-4-yl]aminopropoxy)pyridine-2-carboxamide

Ausbeute 82.1%

Lösungsmittel

N,N-dimethylacetamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solvent was evaporated in vacuo
2. 2
   workup.ADDITIONthe residue was treated with 5% sodium bicarbonate (20 mL) and ethyl acetate (20 mL)
3. 3
   FiltrationThe precipitate was filtered
4. 4
   Waschenwashed with water and ethyl ether
5. 5
   SonstigeThe resulting white solid was purified by column chromatography over silica gel

Vorschrift

A mixture of 4-chloro-5-(1,3-thiazol-2-yl)thieno[2,3-d]pyrimidine (0.050 g, 0.20 mmol), 5-(3-aminopropoxy)-N-methylpyridine-2-carboxamide trifluoroacetate (0.070 g, 0.22 mmol), potassium carbonate (0.272 g, 1.97 mmol) and N,N-dimethylacetamide (2.4 mL) was heated at 120° C. for 13 h. The solvent was evaporated in vacuo, and the residue was treated with 5% sodium bicarbonate (20 mL) and ethyl acetate (20 mL). The precipitate was filtered and washed with water and ethyl ether. The resulting white solid was purified by column chromatography over silica gel to give 70 mg (81%) N-methyl-5-(3-[5-(1,3-thiazol-2-yl)thieno[2,3-d]pyrimidin-4-yl]aminopropoxy)pyridine-2-carboxamide. MS [M+H]=427, LC/MS (EI) tR 3.54 min (Method D), 1H NMR (10% MeOD/CDCl3) δ (ppm) 10.85 (s, 1H), 8.30 (s, 1H), 8.12 (d, J=2.4 Hz, 1H), 8.00 (d, J=8.7 Hz, 1H), 7.94 (b, 1H), 7.71 (s, 1H), 7.50 (d, J=3.6 Hz, 1H), 7.28 (s, 1H), 7.21 (dd, J=8.7, 3.0 Hz, 1H), 4.15 (t, J=0.6 Hz, 2H), 3.80-3.74 (m, 2H), 2.94 (d, J=0.6 Hz, 3H), 2.24-2.18 (m, 2H).

Quelle