Reaktion #2496144

Reaktionsgleichung

KBr

4-chloro-6,7-dimethoxyquinazoline

3-amino-5-tert-butylselenophene-2-carboxamide

NaOH

→

3-(6,7-Dimethoxyquinazolin-4-ylamino)-5-tert-butylselenophene-2-carboxamide

Lösungsmittel

water

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONThe mixture was poured into ice
2. 2
   workup.STIRRINGstirred for 10 min
3. 3
   SonstigeThe solid separated
4. 4
   Filtrationwas filtered
5. 5
   Waschenwashed with water
6. 6
   Sonstigedried (730 mg, 76%)
7. 7
   SonstigeThe crude product was further chromatographed
8. 8
   Sonstigerecrystallized from chloroform-methanol
9. 9
   Sonstigeto give the product as a pale yellow color solid, mp 248-252° C

Vorschrift

To a solution of 4-chloro-6,7-dimethoxyquinazoline (500 mg, 2.23 mmol) in DMF (20 mL) was added sequentially 3-amino-5-tert-butylselenophene-2-carboxamide (820 mg, 3.34 mmol), powdered NaOH (270 mg, 6.69 mmol) and catalytic amount of KI at rt and the mixture was stirred at rt for 16 h. The mixture was poured into ice cooled water and stirred for 10 min. The solid separated was filtered, washed with water and dried (730 mg, 76%). The crude product was further chromatographed and recrystallized from chloroform-methanol to give the product as a pale yellow color solid, mp 248-252° C. IR (KBr) vmax 3470, 3134, 2960, 1626, 1577, 1469, 1385, 1238, 1211, 1133, 1010, 856, 750 cm−1; 1H NMR (400 MHz, DMSO-d6): δ 12.65 (1H, s, exchangeable with D2O), 8.74 (1H, s), 8.62 (1H, s), 7.64 (2H, br s, exchangeable with D2O), 7.36 (1H, s), 7.25 (1H, s), 3.96 (3H, s), 3.95 (3H, s), 1.42 (9H, s); 13C NMR (100 MHz, DMSO-d6): δ 168.3, 167.5, 154.5, 153.8, 152.9, 149.4, 146.9, 146.1, 120.7, 111.8, 108.7, 107.5, 99.8, 55.9, 55.5, 36.5, 32.2; LC-MS (positive ion mode): m/z 433, 435 (M+H)+.

Quelle