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 1865782Notes

Reaction equation

HRID 1865782 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-c0a6a21879984034b8cf2ade0e83704c
Source dataset
uspto-grants-2009_12
Patent number
US07629320B2

Reaction notes

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