Acetaldehyde → HCID 18452869, compound

HRID 1271220Notes

Reaction equation

HRID 1271220 reaction equation
N[C:2]1C=NC=N[CH:7]=1.C(=O)C.[H][H].[CH2:13]([NH:15][C:16]1[CH:17]=[N:18][CH:19]=[N:20][CH:21]=1)[CH3:14]>C(O)C.O=[Pt]=O>[CH2:13]([N:15]([C:16]1[CH:17]=[N:18][CH:19]=[N:20][CH:21]=1)[CH2:2][CH3:7])[CH3:14]

Participants

7

Reactant 4

HCID 177AcetaldehydeHCID 344373Pyrimidin-5-amineHCID 694722071368022-07-4HCID 178418361HCID 178418361, compound

Product 1

HCID 18452869HCID 18452869, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

A suspension of the 5-aminopyrimidine, and one twenty-fifth an equal mass of PtO2, and 5 equivalents equivalents of aqueous acetaldehyde, in ethanol solvent, was shaken under 60 psi hydrogen gas for 24 h. At this time, TLC of an evaporated aliquot of the reaction mixture indicated complete conversion of the 5-(N-ethyl)aminopyrimidine. The Pt catalyst was removed by filtering the reaction mixture through Celite, and the 5-(N,N-diethyl)aminopyrimidine was isolated by evaporation of the ethanol solvent. The crude product was purified by flash chromatography on silica using EtOAc/hexanes.

Workup

  1. customThe Pt catalyst was removed
  2. filtrationby filtering the reaction mixture through Celite

Sources & evidence

ORD record
ord-d24865bc7b22419b8a1bf849372426e2
Source dataset
uspto-grants-2007_04
Patent number
US07205310B2

Reaction notes

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