Diisopropylethylamine → [1-(6-Fluoro-3,4-dihydro-5-oxa-1,2a-diazaacenaphthylen-2-yl)ethyl]-[9-(tetrahydropyran-2-yl)-9H-purin-6-yl]amine

HRID 243225Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 1-(6-fluoro-3,4-dihydro-5-oxa-1,2a-diazaacenaphthylen-2-yl)ethylamine (85 mg, 0.38 mmol), 6-chloro-9-(tetrahydropyran-2-yl)-9H-purine (92 mg, 0.38 mmol) and DIPEA (132 μL, 0.76 mmol) in IPA (1 mL) was heated for 18 h at 100° C. After cooling to RT, the volatiles were removed in vacuo and the resulting residue was purified by column chromatography (Si—PPC, gradient 0-5% MeOH in DCM) to afford the title compound as a pale yellow oil (132 mg, 82%). LCMS (Method J): RT=2.22 min, [M+H]+=424

Workup

temperatureAfter cooling to RT
customthe volatiles were removed in vacuo
customthe resulting residue was purified by column chromatography (Si—PPC, gradient 0-5% MeOH in DCM)

Sources & evidence

ORD record: ord-024c66a09d24420b8036b9a9f57f77c8
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653089B2

Reaction notes

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