1,1'-Carbonyldiimidazole → HCID 123689797, compound

HRID 523258Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:4]([CH2:9][C:10]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([B:19]3[O:23][C:22]([CH3:25])([CH3:24])[C:21]([CH3:27])([CH3:26])[O:20]3)[C:14]=2[CH3:28])=[O:11])=[N:5][CH:6]=[CH:7][CH:8]=1.C1N=CN([C:34](N2C=NC=C2)=[O:35])C=1>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[C:4]2[N:5]([C:34](=[O:35])[N:12]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([B:19]4[O:23][C:22]([CH3:24])([CH3:25])[C:21]([CH3:27])([CH3:26])[O:20]4)[C:14]=3[CH3:28])[C:10](=[O:11])[CH:9]=2)[CH:6]=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 2-(3-methoxypyridin-2-yl)-N-(2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetamide (1.45 g, 3.78 mmol) and CDI (2.45 g, 15.1 mmol) in toluene (19 mL) was heated at 110° C. for 3 h. The cooled mixture was partitioned between EtOAc and water. The organic layer was washed sequentially with water and brine, dried and concentrated. The residue was purified by column chromatography on silica gel, eluting with EtOAc-hexanes, to give 5-methoxy-2-(2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-pyrido[1,2-c]pyrimidine-1,3(2H)-dione as a yellow solid (0.571 g, 37% yield). Mass spectrum m/z 409 (M+H)+. 1H NMR (400 MHz, chloroform-d) δ 7.96 (d, J=7.0 Hz, 1H), 7.91 (dd, J=7.4, 1.2 Hz, 1H), 7.33 (t, J=7.6 Hz, 1H), 7.22 (dd, J=7.8, 1.2 Hz, 1H), 6.39-6.30 (m, 2H), 6.24 (s, 1H), 3.93 (s, 3H), 2.34 (s, 3H), 1.34 (s, 12H).

Workup

customThe cooled mixture was partitioned between EtOAc and water
washThe organic layer was washed sequentially with water and brine
customdried
concentrationconcentrated
customThe residue was purified by column chromatography on silica gel
washeluting with EtOAc-hexanes

Sources & evidence

ORD record: ord-ae63534cd39a48ba90bd1c9b4426cd2f
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09334290B2

Reaction notes

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