Dimethyl Sulfate → HCID 17961790, compound

HRID 1161930Notes

Reaction equation

[H-].[Li+].[CH3:3]OS(OC)(=O)=O.[C:10]([O:18][C:19]1[C:20]([C:40]([O:42][CH3:43])=[O:41])=[N:21][C:22]([C:26]([NH:29][C:30]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:31])([CH3:28])[CH3:27])=[N:23][C:24]=1[OH:25])(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>O1CCOCC1>[C:10]([O:18][C:19]1[C:24](=[O:25])[N:23]([CH3:3])[C:22]([C:26]([NH:29][C:30]([O:32][CH2:33][C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)=[O:31])([CH3:27])[CH3:28])=[N:21][C:20]=1[C:40]([O:42][CH3:43])=[O:41])(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

Conditions

Temperature: 38 °C

Procedure

To a stirred solution of LiH (1.1 eq) in dioxane, methyl 5-(benzoyloxy)-2-(1-{[(benzyloxy)carbonyl]amino}-1-methylethyl)-6-hydroxypyrimidine-4-carboxylate was added and the mixture was stirred at 38° C. for 45 min. After cooling down to room temperature, dimethylsulfate (1.3 eq) was added and reaction mixture was heated at 60° C. for 2 h. Mixture was then cooled to room temperature, dioxane evaporated and residue was purified by flash chromatography, eluting with 65/55 v/v petroleum ether/ethyl acetate. Collection and evaporation of appropriate fractions afforded the title product.

Workup

temperatureAfter cooling down to room temperature
customreaction mixture
temperaturewas heated at 60° C. for 2 h
temperatureMixture was then cooled to room temperature
customdioxane evaporated
customresidue was purified by flash chromatography
washeluting with 65/55 v/v petroleum ether/ethyl acetate
customCollection and evaporation of appropriate fractions

Sources & evidence

ORD record: ord-f43f9ad485554cc08015c3550fbfed81
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820660B2

Reaction notes

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