2-Chloro-6,7-dimethoxy-4-quinazolinamine → 3-Amino-5-[N'-(4-amino-6,7-dimethoxy-quinazolin-2-yl)-hydrazino]-6-chloro-pyrazine-2-carboxylic acid methyl ester

HRID 1274146Notes

Reaction equation

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

Participants

Conditions

Temperature: 120 °C

Procedure

Compound (51) (5 mmol) was added to a solution of 4-amino-2-chloro-6,7-dimethoxy quinazoline (0.96 g, 4 mmol) in isoamyl alcohol (10 mL) at 25° C. The mixture was then stirred at 120° C. for 12 h. After cooling to room temperature, the desired product was filtered and rinsed with acetone to give 1.62 g (96%) of the title compound: TLC (Rf =0.30; 10% CH3OH/CH2Cl2); 1H NMR (DMSO) δ 11.90 (br, 1H), 10.30 (br, 1H), 9.80 (br, 1H), 9.00 (br, 1H), 8.80 (br, 1H), 7.80 (s, 1H), 7.69 (d, 1H, J=2.0), 7.41 (s, 1H), 7.19 (s, 1H), 3.86 (s, 3H), 3.85 (s, 3H), 3.76 (s, 3H); HRMS (FAB) m/z 421.1152 (M+H)+ (C16H18N8O4Cl requires 421.1110); Anal. (C16H18N8O4Cl·1/4CH3OH) C, H, N.

Workup

temperatureAfter cooling to room temperature
filtrationthe desired product was filtered
washrinsed with acetone

Sources & evidence

ORD record: ord-a7aa2f44b54b44b59dc4c8b9c4d396bd
Source dataset: uspto-grants-2000_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06156758

Reaction notes

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