Benzylamine → N-benzylpyrido[4,3-d]pyrimidin-4-amine

HRID 2256144Notes

Reaction equation

HRID 2256144 reaction equation
CS[C:3]1[C:4]2[CH:12]=[N:11][CH:10]=[CH:9][C:5]=2[N:6]=[CH:7][N:8]=1.[CH2:13]([NH2:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CCO>[CH2:13]([NH:20][C:3]1[C:4]2[CH:12]=[N:11][CH:10]=[CH:9][C:5]=2[N:6]=[CH:7][N:8]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 106548874-Methylthiopyrido[4,3-d]pyrimidine

Product 1

HCID 5328247N-benzylpyrido[4,3-d]pyrimidin-4-amineYield 17%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Methylthiopyrido[4,3-d]pyrimidine (160.4 mg, 0.902 mmol), and benzylamine (106.3 mg, 0.992 mmol) in EtOH (2 mL) are heated at 80° C. for 12 h, and then the solvent is removed under reduced pressure. The resulting solid is suspended in CH2Cl2, filtered, and the resulting solid is purified by preparative tlc on silica, eluting with 5% MeOH in CHCl3. Removal of the solvent under reduced pressure yields 4-benzylaminopyrido[4,3-d]pyrimidine (36 mg, 17%). 1H NMR (DMSO) δ 9.60 (1H, s), 9.37 (1H, t, J=5.8 Hz), 8.72 (1H, d, J=5.8 Hz), 8.57 (1H, s), 7.54 (1H, d, J=5.8 Hz), 7.37 (2H, d, J=7.0 Hz), 7.33 (2H, t, J=7.3 Hz), 7.25 (1H, t, J=7.2 Hz), 4.81 (2H, d, J=5.8 Hz).

Workup

  1. customthe solvent is removed under reduced pressure
  2. filtrationfiltered
  3. customthe resulting solid is purified by preparative tlc on silica
  4. washeluting with 5% MeOH in CHCl3
  5. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-f7a83ae9741c4822869dabcfbe747d6c
Source dataset
uspto-grants-1997_08
Patent number
US05654307

Reaction notes

Loading…