2-Chloro-6,7-dimethoxy-4-quinazolinamine → HCID 9889292, compound

HRID 1274120Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[CH:6][CH:5]=1.[NH2:18][C:19]1[C:28]2[C:23](=[CH:24][C:25]([O:31][CH3:32])=[C:26]([O:29][CH3:30])[CH:27]=2)[N:22]=[C:21](Cl)[N:20]=1>C(O)(C)(C)C>[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:5]=[CH:6][C:7]([NH:10][CH:11]2[CH2:16][CH2:15][N:14]([C:21]3[N:20]=[C:19]([NH2:18])[C:28]4[C:23](=[CH:24][C:25]([O:31][CH3:32])=[C:26]([O:29][CH3:30])[CH:27]=4)[N:22]=3)[CH2:13][CH2:12]2)=[CH:8][CH:9]=1

Participants

Conditions

Temperature: 120 °C

Procedure

Compound 47 (0.05 g, 0.21 mmol) was added to a solution of 4-amino-2-chloro-6,7-dimethoxy quinazoline (0.05 g, 0.19 mmol) in tert-butanol (5 mL) at 25° C. The mixture was subsequently stirred at 120° C. for 12 h. The reaction mixture was then cooled to room temperature and the desired product was filtered and rinsed with acetone to give 0.07 g (83%) of the title compound: TLC (Rf =0.35; 5% MeOH/CH2Cl2); 1H NMR (DMSO) δ 12.15 (s, 1H), 8.75 (d, 2H), 7.73 (s, 1H), 7.69 (d, 2H, J=8.7), 7.51 (s, 1H), 6.66 (d, 2H, J=8.4), 6.57 (d, 1H, J=7.3), 4.52 (d, 2H, J=13.2), 3.87 (s, 3H), 3.83 (s, 3H), 3.82 (m, 1H), 3.73 (s, 3H), 3.43 (m, 2H), 2.05 (m, 2H), 1.44 (m, 2H); 13C NMR (CDCl3) δ 166.3, 161.4, 155.2, 151.7, 151.0, 146.7, 136.0, 131.0, 115.8, 111.3, 104.9, 101.6, 99.2, 56.2, 56.0, 51.2, 47.9, 43.4, 31.0; Anal. (C23H27N5O4 ·1HCl) C, H, N.

Workup

temperatureThe reaction mixture was then cooled to room temperature
filtrationthe desired product was filtered
washrinsed with acetone

Sources & evidence

ORD record: ord-a6a8d0e5727d4a7198839d30832f65e1
Source dataset: uspto-grants-2000_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06156758

Reaction notes

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