Water → HCID 58296195, compound

HRID 552774Notes

Reaction equation

HRID 552774 reaction equation
[S:1](=[O:31])(=[O:30])([O:3][CH2:4][C@@H:5]1[C@@H:9]([OH:10])[CH2:8][C@H:7]([N:11]2[C:15]3[N:16]=[CH:17][N:18]=[C:19]([CH2:20][CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[C:14]=3[C:13]([C:28]#[CH:29])=[CH:12]2)[O:6]1)[NH2:2].O>CCO.[Pd]>[S:1](=[O:30])(=[O:31])([O:3][CH2:4][C@@H:5]1[C@@H:9]([OH:10])[CH2:8][C@H:7]([N:11]2[C:15]3[N:16]=[CH:17][N:18]=[C:19]([CH2:20][CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[C:14]=3[C:13]([CH2:28][CH3:29])=[CH:12]2)[O:6]1)[NH2:2]

Participants

5

Reactant 2

HCID 962WaterHCID 58296236HCID 58296236, compound

Product 1

HCID 58296195HCID 58296195, compoundYield 11.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of {(2R,3S,5R)-5-[5-ethynyl-4-(2-phenylethyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]-3-hydroxytetrahydrofuran-2-yl}methyl sulfamate (0.0824 g, 0.190 mmol) and Pd/C (10% wt, ˜50% H2O, 0.01 g) in EtOH (10 mL) was stirred under an atmosphere of H2 (1 atm) for 5 h at r.t. The reaction mixture was filtered through celite and the filtrate was concentrated. The residue was purified by flash chromatography (0 to 10% MeOH/DCM) to give the title compound (0.010 g, 11%).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by flash chromatography (0 to 10% MeOH/DCM)

Sources & evidence

ORD record
ord-dae5897c761a458599496a5294413f16
Source dataset
uspto-grants-2011_05
Patent number
US07951810B2

Reaction notes

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