2-{6-Azido-5-(4-methylphenyl)pyrimidin-4-yloxy}ethanol → 2-{6-Amino-5-(4-methylphenyl)-pyrimidin-4-yloxy}ethanol

HRID 2303

Reaction equation

HRID 2303 reaction equation
[N:1]([C:4]1[N:9]=[CH:8][N:7]=[C:6]([O:10][CH2:11][CH2:12][OH:13])[C:5]=1[C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=1)=[N+]=[N-]>[C].[Pd].C(O)C>[NH2:1][C:4]1[N:9]=[CH:8][N:7]=[C:6]([O:10][CH2:11][CH2:12][OH:13])[C:5]=1[C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=1

Participants

4

Reactant 1

HCID 118077902-{6-Azido-5-(4-methylphenyl)pyrimidin-4-yloxy}ethanol

Product 1

HCID 111182972-{6-Amino-5-(4-methylphenyl)-pyrimidin-4-yloxy}ethanolYield 89.7%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

A mixture of 2-{6-azido-5-(4-methylphenyl)pyrimidin-4-yloxy}-ethanol (19.6 g), 10% palladium-carbon (50% moist) (4.0 g) and ethanol (240 ml) is subjected to catalytic hydrogenation at room temperature under hydrogen atmosphere (1 atm) for one hour. The catalyst is removed by filtration, and the filtrate is concentrated under reduced pressure. The residue is recrystallized from ethyl acetate/n-hexane to give 2-{6-amino-5-(4-methylphenyl)pyrimidin-4-yloxy}ethanol (15.9 g).

Workup

  1. customis subjected to catalytic hydrogenation at room temperature under hydrogen atmosphere
  2. customfor one hour
  3. customThe catalyst is removed by filtration
  4. concentrationthe filtrate is concentrated under reduced pressure
  5. customThe residue is recrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-5cec6056ae4c4169bd4252bc117b2be6
Source dataset
uspto-grants-1998_03
Patent number
US05728706

Linked notes

Loading…