1,1'-Carbonyldiimidazole → HCID 123693342, compound

HRID 523263Notes

Reaction equation

[CH3:1][C:2]1[C:7]([B:8]2[O:12][C:11]([CH3:14])([CH3:13])[C:10]([CH3:16])([CH3:15])[O:9]2)=[CH:6][CH:5]=[CH:4][C:3]=1[NH:17][C:18](=[O:25])[CH2:19][C:20]1[S:21][CH:22]=[CH:23][N:24]=1.C1N=CN([C:31](N2C=NC=C2)=[O:32])C=1>C1(C)C=CC=CC=1>[CH3:1][C:2]1[C:7]([B:8]2[O:12][C:11]([CH3:13])([CH3:14])[C:10]([CH3:16])([CH3:15])[O:9]2)=[CH:6][CH:5]=[CH:4][C:3]=1[N:17]1[C:18](=[O:25])[CH:19]=[C:20]2[S:21][CH:22]=[CH:23][N:24]2[C:31]1=[O:32]

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of N-(2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-2-(thiazol-2-yl)acetamide (0.45 g, 1.26 mmol) and CDI (0.815 g, 5.02 mmol) in toluene (6.5 mL) was heated at 110° C. for 2 h. The cooled mixture was partitioned between EtOAc and water. The organic layer was washed with brine, and the combined aqueous layers were extracted with EtOAc. The combined organic layers were dried and concentrated. The residue was purified by column chromatography on silica gel (40 g), eluting with 70% EtOAc-hexanes, to give slightly impure 6-(2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-5H-thiazolo[3,2-c]pyrimidine-5,7(6H)-dione as a tan solid (34% yield). The material was used without further purification. Mass spectrum m/z 385 (M+H)+.

Workup

customThe cooled mixture was partitioned between EtOAc and water
washThe organic layer was washed with brine
extractionthe combined aqueous layers were extracted with EtOAc
customThe combined organic layers were dried
concentrationconcentrated
customThe residue was purified by column chromatography on silica gel (40 g)
washeluting with 70% EtOAc-hexanes

Sources & evidence

ORD record: ord-4014f34665d94928a2bda0f1a61f114e
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09334290B2

Reaction notes

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