Guanidine → 2-Amino-7-bromoquinazoline

Reaction equation

[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[C:4](F)[CH:3]=1.[NH2:11][C:12]([NH2:14])=[NH:13].CN(C=O)C>O>[Br:1][C:2]1[CH:3]=[C:4]2[C:5]([CH:6]=[N:11][C:12]([NH2:14])=[N:13]2)=[CH:8][CH:9]=1

Participants

Procedure

The 4-Bromo-2-fluoro-benzaldehyde (0.61 g, 3 mmol), guanidine (1.05 g, 5.83 mmol) and DMF were heated at 140° C. for 2.5 hours. 50 ml water was added to the mixture. The orange precipitate was filtered and washed with water. The solid was dissolved in 2N HCl. and filtered. The HCl solution was neutralized by ammonia hydroxyl. The off white solid was filtered and dried under vacuum to afforded the desired product (91 mg, 14%). MS (ESI) m/e 224 (M+1)+; 1H NMR (300 MHz, DMSO-D6) δ ppm 7.00 (br. s., 2 H) 7.36 (d, J=8.82 Hz, 1 H) 7.77 (dd, J=9.16, 2.37 Hz, 1 H) 8.05 (d, J=2.37 Hz, 1 H) 9.09 (br. s., 1 H).