Triethylamine → 5-[4-(7-Methoxy-3-phenyl-imidazo[1,2-a]pyrimidin-2-yl)-phenyl]-2-oxa-4-aza-bicyclo[3.1.1]heptan-3-one

HRID 872300

Reaction equation

Br[CH:2]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]23[CH2:17][CH:15]([CH2:16]2)[O:14][C:13](=[O:18])[NH:12]3)=[CH:7][CH:6]=1)=O.[CH3:25][O:26][C:27]1[CH:32]=[CH:31][N:30]=[C:29]([NH2:33])[N:28]=1.C(N(CC)CC)C>C(O)C>[CH3:25][O:26][C:27]1[CH:32]=[CH:31][N:30]2[C:2]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[C:3]([C:5]3[CH:10]=[CH:9][C:8]([C:11]45[CH2:17][CH:15]([CH2:16]4)[O:14][C:13](=[O:18])[NH:12]5)=[CH:7][CH:6]=3)[N:33]=[C:29]2[N:28]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of crude 5-[4-(2-bromo-2-phenyl-acetyl)-phenyl]-2-oxa-4-aza-bicyclo[3.1.1]heptan-3-one (2.5 g), 4-methoxypyrimidin-2-amine (1.26 g), triethylamine (0.84 mL) and ethanol (62 mL), under argon, was heated at 100° C. (bath temperature) for 6 hours. On cooling the reaction was concentrated and partitioned between EtOAc and water. The aqueous phase was extracted with EtOAc and the combined organic phases were washed with brine, dried and concentrated. Purification was achieved by chromatography on silica gel followed by preparative reverse phase HPLC to give the title compound.

Workup

temperatureOn cooling the reaction
concentrationwas concentrated
custompartitioned between EtOAc and water
extractionThe aqueous phase was extracted with EtOAc
washthe combined organic phases were washed with brine
customdried
concentrationconcentrated
customPurification

Sources & evidence

ORD record: ord-b35483ed864f417a9415f319200dab38
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08975265B2

Linked notes

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