Benzylamine → 2-aminopyrido[2,3-d]pyrimidin-7(8H)-one 27

HRID 3187

Reaction equation

HRID 3187 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:20](=[O:21])[N:19]([CH3:22])[C:12]2[N:13]=[C:14](SC)[N:15]=[CH:16][C:11]=2[CH:10]=1.[CH2:23]([NH2:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN(C)C=O>[CH2:23]([NH:30][C:14]1[N:15]=[CH:16][C:11]2[CH:10]=[C:9]([C:3]3[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=3[Cl:8])[C:20](=[O:21])[N:19]([CH3:22])[C:12]=2[N:13]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 107367016-(2,6-Dichlorophenyl)-8-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one

Product 1

HCID 53278742-aminopyrido[2,3-d]pyrimidin-7(8H)-one 27Yield 47.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 0.165 g (0.47 mmol) of 6-(2,6-dichlorophenyl)-8-methyl-2-methylsulfanyl-8H-pyrido-[2,3-d]pyrimidin-7-one of Example 37, 0.50 g (4.70 mmol) of benzylamine and 0.5 mL of dimethylformamide was heated with stirring in a 120° C. oil bath. After 5 minutes, solution was complete. After 5 hours, the excess amine and dimethylformamide were evaporated at reduced pressure, and the residue was triturated with a solution of 1 mL of acetone and 2 mL of petroleum ether. The tacky solid was filtered and recrystallized from ethyl acetate/petroleum ether to give 0.092 g of pure product; mp 217°-219° C.

Workup

  1. temperaturewas heated
  2. waitAfter 5 hours
  3. customthe excess amine and dimethylformamide were evaporated at reduced pressure
  4. customthe residue was triturated with a solution of 1 mL of acetone and 2 mL of petroleum ether
  5. filtrationThe tacky solid was filtered
  6. customrecrystallized from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-25e5f36c73a5443aa2d8d2b4bbb40382
Source dataset
uspto-grants-1998_03
Patent number
US05733914

Linked notes

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