Potassium Carbonate → HCID 69421997, compound

HRID 916590Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([CH2:7][C:8]2[C:9](=[O:16])[NH:10][C:11]([CH3:15])=[N:12][C:13]=2[CH3:14])=[CH:5][CH:4]=1.[CH3:19][C:20]([O:22][CH2:23][C@H:24]1[O:29][C@H:28](Br)[C@H:27]([O:31][C:32]([CH3:34])=[O:33])[C@@H:26]([O:35][C:36]([CH3:38])=[O:37])[C@@H:25]1[O:39][C:40]([CH3:42])=[O:41])=[O:21].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:32]([O:31][C@@H:27]1[C@@H:26]([O:35][C:36](=[O:37])[CH3:38])[C@H:25]([O:39][C:40](=[O:41])[CH3:42])[C@@H:24]([CH2:23][O:22][C:20](=[O:21])[CH3:19])[O:29][C@H:28]1[O:16][C:9]1[C:8]([CH2:7][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:18][CH:17]=2)=[C:13]([CH3:14])[N:12]=[C:11]([CH3:15])[N:10]=1)(=[O:33])[CH3:34]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 5-(4-methoxybenzyl)-2,6-dimethyl-3H-pyrimidin-4-one (0.30 g) in acetonitrile (6 mL) were added acetobromo-α-D-glucose (0.76 g) and potassium carbonate (0.27 g), and the mixture was stirred for 17 hours at 60° C. The insoluble material was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on aminopropyl silica gel (eluent: hexane/ethyl acetate=1/1) and on silica gel (eluent: hexane/ethyl acetate=1/1-1/2) to give 4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-5-(4-methoxybenzyl)-2,6-dimethylpyrimidine (0.24 g).

Workup

customThe insoluble material was removed by filtration
concentrationthe filtrate was concentrated under reduced pressure
customThe residue was purified by column chromatography on aminopropyl silica gel (eluent: hexane/ethyl acetate=1/1) and on silica gel (eluent: hexane/ethyl acetate=1/1-1/2)

Sources & evidence

ORD record: ord-9a5fe0ab25c74b24850f678ae85e5035
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07271153B2

Reaction notes

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