Water → 8-Azido-5-(quinolin-3-yl)-6,7,8,9-tetrahydropyrimido[5,4-b]indolizin-4-amine

HRID 336141Notes

Reaction equation

[N-:1]=[N+:2]=[N-:3].[Na+].CS(O[CH:10]1[CH2:18][CH2:17][C:16]2[N:12]([C:13]3[N:32]=[CH:31][N:30]=[C:29]([NH2:33])[C:14]=3[C:15]=2[C:19]2[CH:20]=[N:21][C:22]3[C:27]([CH:28]=2)=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:11]1)(=O)=O.O>CN(C=O)C>[N:1]([CH:10]1[CH2:18][CH2:17][C:16]2[N:12]([C:13]3[N:32]=[CH:31][N:30]=[C:29]([NH2:33])[C:14]=3[C:15]=2[C:19]2[CH:20]=[N:21][C:22]3[C:27]([CH:28]=2)=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:11]1)=[N+:2]=[N-:3]

Participants

Conditions

Temperature: 80 °C

Procedure

Sodium azide (361 mg) was added to a solution of 4-amino-5-(quinolin-3-yl)-6,7,8,9-tetrahydropyrimido[5,4-b]indolizin-8-yl methanesulfonate (758 mg) obtained in Step 9 in DMF (9 ml) at room temperature, and the mixture was stirred at 80° C. for 4 hours. After cooling, the reaction mixture was poured into water, followed by extraction with ethyl acetate. The organic layer was washed with water and a saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain the title compound as a yellow solid (508 mg).

Workup

temperatureAfter cooling
extractionfollowed by extraction with ethyl acetate
washThe organic layer was washed with water
dry with materiala saturated sodium chloride solution, and dried over anhydrous sodium sulfate
distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record: ord-21f0adb07a4a460ea9c3f56ae98b71de
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889666B2

Reaction notes

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