Dimethyl Sulfoxide → HCID 67150585, compound

HRID 2220862Notes

Reaction equation

OC[CH:3]1[CH:7]2[O:8][C:9]([CH3:12])([CH3:11])[O:10][CH:6]2[CH:5]([N:13]2[CH:21]=[N:20][C:19]3[C:14]2=[N:15][CH:16]=[N:17][C:18]=3[NH:22][C:23]([NH:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:24])[O:4]1.[C:32]([O:35][CH2:36]C)(=[O:34])[CH3:33].[CH3:38]S(C)=O>>[CH3:36][O:35][C:32](=[O:34])[CH:33]=[CH:38][CH:3]1[CH:7]2[CH:6]([O:10][C:9]([CH3:11])([CH3:12])[O:8]2)[CH:5]([N:13]2[CH:21]=[N:20][C:19]3[C:14]2=[N:15][CH:16]=[N:17][C:18]=3[NH:22][C:23]([NH:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)=[O:24])[O:4]1

Participants

Reactant 3

HCID 679Dimethyl Sulfoxide

HCID 8857Ethyl Acetate

HCID 67150697HCID 67150697, compound

Product 1

HCID 67150585HCID 67150585, compound

Procedure

To a vial containing the starting compound, 1-[9-(6-Hydroxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-yl]-3-phenyl-urea (1.07 g, 2.5 mmol), in 10 ml of dimethylsulfoxide was added IBX (1.06 g, 3.75 mmol) in one portion at RT. The white solid gradually dissolved as the reaction proceeded. After stirring at RT for 2 hours, methyl(triphenylphosphorylidene) acetate (0.84 g, 2.5 mmol) was added in one portion. The reaction was run at RT overnight. To the reaction mixture was added ethyl acetate (100 ml), which was washed with saturated NaHCO3, brine, and dried over MgSO4. After removal of solvent, the residue was recrystallized with isopropyl alcohol to provide the title compound. MW calculated for C23H24N6O6 (MH+) 481.5 found 481.3 by LCMS.

Workup

dissolutionThe white solid gradually dissolved as the reaction
waitThe reaction was run at RT overnight
washwas washed with saturated NaHCO3, brine
dry with materialdried over MgSO4
customAfter removal of solvent
customthe residue was recrystallized with isopropyl alcohol

Sources & evidence

ORD record: ord-0e258c34fcad445aa2b8fddb96e88f7e
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07368438B2

Reaction notes

Loading…