HCID 86624407, compound → HCID 68420239, compound

HRID 657754Notes

Reaction equation

HRID 657754 reaction equation
[N:1]([C@@H:4]([C:14]1[CH:15]=[N:16][C:17]([O:20][CH3:21])=[N:18][CH:19]=1)[CH2:5][O:6][Si:7]([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8])=[N+]=[N-]>C(OCC)(=O)C.[Pd]>[Si:7]([O:6][CH2:5][C@H:4]([C:14]1[CH:19]=[N:18][C:17]([O:20][CH3:21])=[N:16][CH:15]=1)[NH2:1])([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8]

Participants

4

Reactant 1

HCID 86624407HCID 86624407, compound

Product 1

HCID 68420239HCID 68420239, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (S)-5-(1-azido-2-(tert-butyldimethylsilyloxy)ethyl)-2-methoxypyrimidine (11.7 g, 37.7 mmol) in ethyl acetate (300 mL), and 10% Pd—C (70 mg) was stirred under H2 (1 atm) overnight. The catalyst was filtered off and the filtrate was concentrated to yield a light oil. The residue was purified by silica gel chromatography (0-50% MeOH/EtOAc) to afford a colorless oil.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated
  3. customto yield a light oil
  4. customThe residue was purified by silica gel chromatography (0-50% MeOH/EtOAc)
  5. customto afford a colorless oil

Sources & evidence

ORD record
ord-7a765d485faa42c595e5aad4e8be7123
Source dataset
uspto-grants-2011_12
Patent number
US08076345B2

Reaction notes

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