Dimethyl Sulfoxide → HCID 67150585, compound

HRID 735216Notes

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 coin pound, 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-7637724c5931433db97cf5826a6a5595
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592445B2

Reaction notes

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