Methylamine → N8-methyl-5-(quinolin-3-yl)-6,7,8,9-tetrahydropyrimido[5,4-b]indolizine-4,8-diamine

HRID 336145Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

4-Amino-5-(quinolin-3-yl)-6,7,8,9-tetrahydropyrimido[5,4-b]indolizin-8-yl methanesulfonate (30 mg) obtained in Step 9 of Example 1 was dissolved in a solution of methylamine in 40% methanol (1 ml). The solution was stirred at 60° C. for 1 hour and at 80° C. for 22 hours. After cooling, the reaction mixture was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (developing solvent: ethyl acetate/methanol) to obtain the title compound as a light-yellow, oily substance (8.1 mg).

Workup

temperatureAfter cooling
concentrationthe reaction mixture was concentrated under reduced pressure
customThe resulting residue was purified by silica gel column chromatography (developing solvent: ethyl acetate/methanol)

Sources & evidence

ORD record: ord-fb009346b62a4df2a2126169493f8ee8
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889666B2

Reaction notes

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