1,4-Dioxane → HCID 86712035, compound

HRID 2361629Notes

Reaction equation

[C:1]([O:4][C@H:5]1[C@H:9]([O:10][C:11](=[O:13])[CH3:12])[C@@H:8]([CH2:14][O:15][C:16](=[O:18])[CH3:17])[O:7][C@H:6]1[N:19]1[CH:24]=[C:23](I)[C:22](=[O:26])[NH:21][C:20]1=[O:27])(=[O:3])[CH3:2].[CH3:28][Sn:29][CH3:30].O1CCOC[CH2:32]1>>[C:1]([O:4][C@H:5]1[C@H:9]([O:10][C:11](=[O:13])[CH3:12])[C@@H:8]([CH2:14][O:15][C:16](=[O:18])[CH3:17])[O:7][C@H:6]1[N:19]1[CH:24]=[C:23]([Sn:29]([CH3:32])([CH3:30])[CH3:28])[C:22](=[O:26])[NH:21][C:20]1=[O:27])(=[O:3])[CH3:2]

Participants

Reactant 3

HCID 312751,4-Dioxane

HCID 31651Dimethyltin

HCID 11540528HCID 11540528, compound

Product 1

HCID 86712035HCID 86712035, compound

Conditions

Temperature: 100 °C

Procedure

600 mg (1.21 mmol) of the above compound 5 as a starting material, 1.42 g (4.32 mmol, 3.6 eq) of dimethyl tin (Sn2Me6) and 22 mg (0.03 eq) of bis-triphenylphosphine palladium dichloride are dissolved in 36 mL of 1,4-dioxane, with continuously stirring at 100° C. After the starting material disappears, the solution is concentrated under reduced pressure, and then purified by rapid column chromatography (EtOAc/n-hexane=1:1). A white solid product (1-(2′,3′,5′-Tri-O-acetyl-β-D-arabinofuranosyl)-5-trimethylstannylpyrimidin-2,4(3H)-dione) 6 is obtained. Its weight and yield are 500 mg and 75%, respectively.

Workup

concentrationthe solution is concentrated under reduced pressure
custompurified by rapid column chromatography (EtOAc/n-hexane=1:1)

Sources & evidence

ORD record: ord-c5fce2c145b9480281766ccc7659be01
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691789B2

Reaction notes

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