2-Chloro-6,7-dimethoxy-4-quinazolinamine → HCID 9933665, compound

HRID 1274125Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[C:10]([NH2:11])=[N:9][C:8]([NH:12][CH:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[CH:7][N:6]=1)=[O:4].[NH2:19][C:20]1[C:29]2[C:24](=[CH:25][C:26]([O:32][CH3:33])=[C:27]([O:30][CH3:31])[CH:28]=2)[N:23]=[C:22](Cl)[N:21]=1>C(O)CC(C)C>[CH3:1][O:2][C:3]([C:5]1[C:10]([NH2:11])=[N:9][C:8]([NH:12][CH:13]2[CH2:18][CH2:17][N:16]([C:22]3[N:21]=[C:20]([NH2:19])[C:29]4[C:24](=[CH:25][C:26]([O:32][CH3:33])=[C:27]([O:30][CH3:31])[CH:28]=4)[N:23]=3)[CH2:15][CH2:14]2)=[CH:7][N:6]=1)=[O:4]

Participants

Conditions

Temperature: 120 °C

Procedure

Compound (38) (2.5 mmol) was added to a solution of 4-amino-2-chloro-6,7-dimethoxyquinazoline (0.6 g, 2.5 mmol) in isoamyl alcohol (20 mL) at 25° C. The mixture was 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 0.70 g (65%) of the title compound: TLC (Rf =0.30; 10% CH3OH/CH2Cl2); 1H NMR (DMSO) δ 7.59 (d, 1H, J=7.7), 7.41 (s, 1H), 7.22 (s, 1H), 7.15 (br s, 4H), 6.73 (s, 1H), 4.63 (d, 2H, J=13.2), 4.10 (m, 1H), 3.82 (s, 3H), 3.77 (s, 3H), 3.69 (s, 3H), 2.99 (t, 2H, J=9.8), 1.90 (d, 2H, J=10.0), 1.39 (m, 2H); 13C NMR (DMSO) δ 167.0, 31.2; HRMS (FAB) m/z 455.2143 (M+H)+ (C21H26N8O4 requires 455.2155); Anal. (C21H26N8O4 ·1/2H2O·1/2CH3OH) 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-5d5351b38c4942ac96cbe172a6789921
Source dataset: uspto-grants-2000_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06156758

Reaction notes

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