Reaktion #2496152

Reaktionsgleichung

3-(6-aminoquinazolin-4-ylamino)-5-tert-butylselenophene-2-carboxamide

chloroacetyl chloride

→

solid

Ausbeute 88.7%

3-(6-(2-chloroacetamido)quinazolin-4-ylamino)-5-tert-butylselenophene-2-carboxamide

Ausbeute 88.7%

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstige(solid separated)
2. 2
   workup.ADDITIONThe solution was poured into ice cold water
3. 3
   workup.STIRRINGstirred for 15 min
4. 4
   FiltrationThe separated solid was filtered
5. 5
   Waschenwashed with water
6. 6
   Sonstigedried

Vorschrift

To a solution of 3-(6-aminoquinazolin-4-ylamino)-5-tert-butylselenophene-2-carboxamide (510 mg, 1.31 mmol) in THF (10 mL) was added a solution of chloroacetyl chloride (0.105 mL, 1.31 mmol) in THF (1.0 mL) at rt. The mixture was stirred at rt for 30 min (solid separated). The solution was poured into ice cold water and stirred for 15 min. The separated solid was filtered, washed with water and dried to give the product as a yellow color solid (540 mg, 80%). This crude product was further chromatographed and recrystallized from chloroform-methanol. Mp 262-264° C.; IR (KBr) vmax 3437, 3109, 2961, 1706, 1652, 1608, 1575, 1541, 1464, 1386, 1355, 1311, 1241, 1137, 1086, 858, 834, 790 cm−1; 1H NMR (400 MHz, DMSO-d6): δ 12.79 (1H, s, exchangeable with D2O), 10.83 (1H, s, exchangeable with D2O), 8.83 (1H, s), 8.73 (1H, s), 8.60 (1H, br s), 8.01-8.03 (1H, m), 7.89 (1H, d, J=8.8 Hz), 7.68 (2H, br s), 4.41 (2H, s), 1.47 (9H, s); 13C NMR (100 MHz, DMSO-d6): δ 167.9, 167.2, 164.9, 154.9, 153.2, 146.3, 145.5, 137.2, 128.7, 126.7, 121.1, 115.2, 113.1, 110.0, 43.3, 36.5, 32.2; LC-MS (negative ion mode): m/z 462, 464, 466 (M−H)−.

Quelle