2-(4-Tert-butylphenyl)ethan-1-amine → 4-[2-[4-(t-Butyl)phenyl]ethylamino]pyrido[4,3-d]pyrimidine

HRID 2226837Notes

Reaction equation

HRID 2226837 reaction equation
[N:1]1[C:6]2[CH:7]=[CH:8][N:9]=[CH:10][C:5]=2[C:4](O)=[N:3][CH:2]=1.[C:12]([C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][NH2:24])=[CH:18][CH:17]=1)([CH3:15])([CH3:14])[CH3:13]>C[Si](C)(C)N[Si](C)(C)C>[C:12]([C:16]1[CH:17]=[CH:18][C:19]([CH2:22][CH2:23][NH:24][C:4]2[C:5]3[CH:10]=[N:9][CH:8]=[CH:7][C:6]=3[N:1]=[CH:2][N:3]=2)=[CH:20][CH:21]=1)([CH3:15])([CH3:13])[CH3:14]

Participants

4

Reactant 2

HCID 27356892-(4-Tert-butylphenyl)ethan-1-amineHCID 178518024HCID 178518024, compound

Product 1

HCID 189637984-[2-[4-(t-Butyl)phenyl]ethylamino]pyrido[4,3-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 13838HexamethyldisilazaneSolvent

Procedure

A mixture consisting of 0.45 g of pyrido[4,3-d]pyrimidine-4-ol, 0.53 g of 2-[4-(t-butyl)phenyl]ethylamine, about 40 mg of (NH4)2SO4 in 4 mL of hexamethyldisilazane was refluxed for about five hours. The mixture was then cooled and excess disilazane was removed in vacuo. The residue was dissolved in CH2Cl2, and the solution was washed with water and filtered through phase separating paper. Evaporated the CH2Cl2 and adsorbed the residue onto silica gel, which was applied to a thin silica pad and eluted with CH2Cl2 →50% EtOAc/50% CH2Cl2 →EtOAc. Fractions containing the major product were combined and the product which crystallized was recrystallized from hexane/EtOAc. Yield 0.2 g. M.P. 157°-158° C.

Workup

  1. temperaturewas refluxed for about five hours
  2. temperatureThe mixture was then cooled
  3. customexcess disilazane was removed in vacuo
  4. dissolutionThe residue was dissolved in CH2Cl2
  5. washthe solution was washed with water
  6. filtrationfiltered through phase
  7. customseparating paper
  8. customEvaporated the CH2Cl2
  9. washeluted with CH2Cl2 →50% EtOAc/50% CH2Cl2
  10. additionFractions containing the major product
  11. customthe product which crystallized
  12. customwas recrystallized from hexane/EtOAc

Sources & evidence

ORD record
ord-19dfb3c7e6c440c9aa44ad8c3f4a0add
Source dataset
uspto-grants-1994_09
Patent number
US05350749

Reaction notes

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