O-(Trimethylsilyl)hydroxylamine → 2-(4-Hydroxyamino-5-oxazol-5-yl-pyrrolo[2,3-d]pyrimidin-7-yl)-5-hydroxymethyl-3-methyl-tetrahydro-furan-3,4-diol

HRID 30967

Reaction equation

HRID 30967 reaction equation
Cl[C:2]1[C:3]2[C:10]([C:11]3[O:15][CH:14]=[N:13][CH:12]=3)=[CH:9][N:8]([CH:16]3[C:20]([CH3:22])([OH:21])[CH:19]([OH:23])[CH:18]([CH2:24][OH:25])[O:17]3)[C:4]=2[N:5]=[CH:6][N:7]=1.C[Si](C)(C)[O:28][NH2:29]>C(O)C>[OH:28][NH:29][C:2]1[C:3]2[C:10]([C:11]3[O:15][CH:14]=[N:13][CH:12]=3)=[CH:9][N:8]([CH:16]3[C:20]([CH3:22])([OH:21])[CH:19]([OH:23])[CH:18]([CH2:24][OH:25])[O:17]3)[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 2734666O-(Trimethylsilyl)hydroxylamineHCID 866235892-(4-Chloro-5-oxazol-5-yl-pyrrolo[2,3-d]pyrimidin-7-yl)-5-hydroxymethyl-3-methyl-tetrahydro-furan-3,4-diol

Product 1

HCID 725629862-(4-Hydroxyamino-5-oxazol-5-yl-pyrrolo[2,3-d]pyrimidin-7-yl)-5-hydroxymethyl-3-methyl-tetrahydro-furan-3,4-diol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The compound from Step 2 is suspended in dry ethanol and O-trimethylsilyl hydroxylamine (10 eq.) is added. The mixture is refluxed for 2 h, evaporated and the crude mixture purified by RP HPLC on a Phenominex column (250×20 mm) using a gradient of acetonitrile in water from 0 to 30% over 30 minutes at 10 mL/minute to yield the title compound.

Workup

  1. temperatureThe mixture is refluxed for 2 h
  2. customevaporated
  3. customthe crude mixture purified by RP HPLC on a Phenominex column (250×20 mm)
  4. customover 30 minutes

Sources & evidence

ORD record
ord-d9827e1b6c9b4e9983e0a8ae85e58b4c
Source dataset
uspto-grants-2008_09
Patent number
US07425547B2

Linked notes

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