Butylamine → 3-Butylamino-6-(2,6-dichlorophenyl)-8-methyl-8H-pyrido[2,3-d]pyrimidin-7-one

HRID 3186

Reaction equation

HRID 3186 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]([NH2:27])[CH2:24][CH2:25][CH3:26]>CN(C)C=O>[CH2:23]([NH:27][N:15]1[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][CH2:14]1)[CH2:24][CH2:25][CH3:26]

Participants

4

Reactant 2

HCID 8007ButylamineHCID 107367016-(2,6-Dichlorophenyl)-8-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one

Product 1

HCID 867523433-Butylamino-6-(2,6-dichlorophenyl)-8-methyl-8H-pyrido[2,3-d]pyrimidin-7-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 0.177 g (0.50 mmol) of 6-(2,6-dichlorophenyl)-8-methyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one of Example 37, 10 mL of n-butylamine and 1.0 mL of dimethylformamide was heated with stirring to reflux (110° C. oil bath). After 1 hour, solution was complete. After 20 hours reflux, the excess amine and dimethylformamide were evaporated, and the residue was triturated with water, filtered, washed with water, and dried; wt 0.180 g. Recrystallization from ethyl acetate/petroleum ether gave pure product; wt 0.116 g; mp 184°-186° C.

Workup

  1. temperaturewas heated
  2. temperatureAfter 20 hours reflux
  3. customthe excess amine and dimethylformamide were evaporated
  4. customthe residue was triturated with water
  5. filtrationfiltered
  6. washwashed with water
  7. customdried
  8. customRecrystallization from ethyl acetate/petroleum ether
  9. customgave pure product

Sources & evidence

ORD record
ord-a8f31c3f69e44f889459e4fbf80bb158
Source dataset
uspto-grants-1998_03
Patent number
US05733914

Linked notes

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