4-Aminopyridine → HCID 22125176, compound

HRID 1858214Notes

Reaction equation

HRID 1858214 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[CH2:18][C:17]2[C:12](=[N:13][C:14](S(C)(=O)=O)=[N:15][CH:16]=2)[N:11]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:10]1=[O:29].[NH2:30][C:31]1[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=1>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[CH2:18][C:17]2[C:12](=[N:13][C:14]([NH:30][C:31]3[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=3)=[N:15][CH:16]=2)[N:11]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:10]1=[O:29]

Participants

4

Reactant 2

HCID 17274-AminopyridineHCID 22125142HCID 22125142, compound

Product 1

HCID 22125176HCID 22125176, compoundYield 15.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 100 mg (0.22 mmol) of 3-(2,6-dichlorophenyl)-7-methanesulfonyl-1-phenyl-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one and 200 mg (2.12 mmol) of 4-aminopyridine in 2 ml of dichloromethane was stirred at room temperature overnight. The mixture was evaporated and the residue was purified by flash column chromatography on silica gel using 10% methanol/dichloromethane for the elution. Product containing fractions were combined and evaporated to give 16 mg (15%) of 3-(2,6-dichlorophenyl)-3,4-dihydro-1-phenyl-7-[(4-pyridyl)amino]pyrimido[4,5-d]pyrimidin-2(1H)-one as an off-white solid which decomposed at 289° C.

Workup

  1. customThe mixture was evaporated
  2. customthe residue was purified by flash column chromatography on silica gel using 10% methanol/dichloromethane for the elution
  3. additionProduct containing fractions
  4. customevaporated

Sources & evidence

ORD record
ord-4e63b4176c354698ab30599af05be4c8
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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