3-Methyl-4-methoxybenzenamine → 2-aminopyrido[2,3-d]pyrimidin-7(8H)-one 53

HRID 3203Notes

Reaction equation

HRID 3203 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:22](=[O:23])[N:21]([CH3:24])[C:12]2[N:13]=[C:14](S(C)(=O)=O)[N:15]=[CH:16][C:11]=2[CH:10]=1.[CH3:25][C:26]1[CH:27]=[C:28]([CH:30]=[CH:31][C:32]=1[O:33][CH3:34])[NH2:29]>CCOCC>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:22](=[O:23])[N:21]([CH3:24])[C:12]2[N:13]=[C:14]([NH:29][C:28]3[CH:30]=[CH:31][C:32]([O:33][CH3:34])=[C:26]([CH3:25])[CH:27]=3)[N:15]=[CH:16][C:11]=2[CH:10]=1

Participants

4

Reactant 2

HCID 672973-Methyl-4-methoxybenzenamineHCID 105961576-(2,6-Dichlorophenyl)-8-methyl-2-methylsulfonyl-8H-pyrido[2,3-d]pyrimidin-7-one

Product 1

HCID 53278992-aminopyrido[2,3-d]pyrimidin-7(8H)-one 53

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
165 °C

Procedure

A mixture of 0.113 g (0.29 mmol) of 6-(2,6-dichlorophenyl)-2-methanesulfonyl-8-methyl-8H-pyrido[2,3-d]pyrimidin-7-one of Example 39 and 0.40 g (2.90 mmol) of 3-methyl-4-methoxyaniline was heated, with stirring, in a 165° C. oil bath. The resulting solution was heated for 5 minutes and cooled to room temperature. Ether (1 mL) was added. The crystals that developed were filtered and washed with 2 mL of ether; wt 0.109 g. The solid was purified to remove dark colors by silica gel chromatography, eluting with chloroform and then ethyl acetate. The ethyl acetate eluent was concentrated to 3 mL volume. On cooling, pure crystals of product separated; wt 0.060 g; mp 218°-220° C.

Workup

  1. temperaturewas heated
  2. temperatureThe resulting solution was heated for 5 minutes
  3. temperaturecooled to room temperature
  4. filtrationThe crystals that developed were filtered
  5. washwashed with 2 mL of ether
  6. customThe solid was purified
  7. customto remove dark colors by silica gel chromatography
  8. washeluting with chloroform
  9. concentrationThe ethyl acetate eluent was concentrated to 3 mL volume
  10. temperatureOn cooling
  11. custompure crystals of product separated

Sources & evidence

ORD record
ord-eda16d28ddde4d29b868c0f9438c5f73
Source dataset
uspto-grants-1998_03
Patent number
US05733914

Reaction notes

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