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

HRID 2287713Notes

Reaction equation

HRID 2287713 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-4e4874cbe9ab411891e97829bd8f327f
Source dataset
uspto-grants-2000_07
Patent number
US06084095

Reaction notes

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