5-(4-Methylpiperazin-1-yl)pentan-1-amine → 2-aminopyrido[2,3-d]pyrimidin-7(8H)-one 33

HRID 3210Notes

Reaction equation

HRID 3210 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.[NH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][N:29]1[CH2:34][CH2:33][N:32]([CH3:35])[CH2:31][CH2:30]1>O>[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]([NH:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][N:29]3[CH2:30][CH2:31][N:32]([CH3:35])[CH2:33][CH2:34]3)[N:15]=[CH:16][C:11]=2[CH:10]=1

Participants

4

Reactant 2

HCID 71384635-(4-Methylpiperazin-1-yl)pentan-1-amineHCID 107367016-(2,6-Dichlorophenyl)-8-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one

Product 1

HCID 53278802-aminopyrido[2,3-d]pyrimidin-7(8H)-one 33

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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 and 0.50 g (2.70 mmol) of 1-(5-aminopentyl)-4-methylpiperazine was heated with stirring in a 180° C. to 185° C. oil bath. After 2 minutes, solution was complete. After 0.5 hour, the solution was cooled to room temperature, and 5 mL of water was added to precipitate a taffy-like gum. Decanted and triturated gum again with 5 mL of water. Decanted and took up gum into 35 mL of ether. The ether solution was washed with 2×50 mL of water, dried (potassium carbonate), and concentrated to 5 mL volume. Petroleum ether was added to slight turbidity. The crystals that separated on inducement were filtered and washed with 80% ether/petroleum ether; wt 0.060 g; mp 110°-112° C.;

Workup

  1. temperaturewas heated
  2. waitAfter 0.5 hour
  3. customto precipitate a taffy-like gum
  4. customDecanted
  5. customtriturated gum again with 5 mL of water
  6. customDecanted
  7. washThe ether solution was washed with 2×50 mL of water
  8. dry with materialdried (potassium carbonate)
  9. concentrationconcentrated to 5 mL volume
  10. additionPetroleum ether was added to slight turbidity
  11. customThe crystals that separated on inducement
  12. filtrationwere filtered
  13. washwashed with 80% ether/petroleum ether

Sources & evidence

ORD record
ord-792d4796913a47ddb4ef1bb450d8932d
Source dataset
uspto-grants-1998_03
Patent number
US05733914

Reaction notes

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