2-(5-Ethynyl-4-hydroxyamino-pyrrolo[2,3-d]pyrimidin-7-yl)-5-hydroxymethyl-3-methyl-tetrahydro-furan-3,4-diol → 2-(4-Hydroxyamino-5-vinyl-pyrrolo[2,3-d]pyrimidin-7-yl)-5-hydroxymethyl-3-methyl-tetrahydro-furan-3,4-diol

HRID 30965Notes

Reaction equation

HRID 30965 reaction equation
[C:1]([C:3]1[C:11]2[C:10]([NH:12][OH:13])=[N:9][CH:8]=[N:7][C:6]=2[N:5]([CH:14]2[C:18]([CH3:20])([OH:19])[CH:17]([OH:21])[CH:16]([CH2:22][OH:23])[O:15]2)[CH:4]=1)#[CH:2].[H][H]>C1COCC1.[Pd].CC([O-])=O.CC([O-])=O.[Pb+2]>[OH:13][NH:12][C:10]1[C:11]2[C:3]([CH:1]=[CH2:2])=[CH:4][N:5]([CH:14]3[C:18]([CH3:20])([OH:19])[CH:17]([OH:21])[CH:16]([CH2:22][OH:23])[O:15]3)[C:6]=2[N:7]=[CH:8][N:9]=1

Participants

5

Reactant 2

HCID 210408352-(5-Ethynyl-4-hydroxyamino-pyrrolo[2,3-d]pyrimidin-7-yl)-5-hydroxymethyl-3-methyl-tetrahydro-furan-3,4-diolHCID 178418361HCID 178418361, compound

Product 1

HCID 210408282-(4-Hydroxyamino-5-vinyl-pyrrolo[2,3-d]pyrimidin-7-yl)-5-hydroxymethyl-3-methyl-tetrahydro-furan-3,4-diol

Reagents, catalysts & solvents 2

HCID 131709914Lindlars catalystCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The title compound from Example 29 is dissolved in THF and placed under hydrogen (1 atm) in the presence of Lindlar's catalyst until one mole of hydrogen is consumed.

Workup

  1. customis consumed

Sources & evidence

ORD record
ord-f9c19a0ec1e048cab0e3cb38330568f2
Source dataset
uspto-grants-2008_09
Patent number
US07425547B2

Reaction notes

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