4-(4-Methylpiperazin-1-yl)aniline → HCID 5330252, compound

HRID 2300063Notes

Reaction equation

HRID 2300063 reaction equation
[CH:1]([N:4]1[C:9]2[N:10]=[C:11](S(C)=O)[N:12]=[CH:13][C:8]=2[CH:7]=[CH:6][C:5]1=[O:17])([CH3:3])[CH3:2].[CH3:18][N:19]1[CH2:24][CH2:23][N:22]([C:25]2[CH:31]=[CH:30][C:28]([NH2:29])=[CH:27][CH:26]=2)[CH2:21][CH2:20]1.[O-2].[Al+3].[O-2].[O-2].[Al+3]>C(Cl)(Cl)Cl>[CH:1]([N:4]1[C:9]2[N:10]=[C:11]([NH:29][C:28]3[CH:27]=[CH:26][C:25]([N:22]4[CH2:21][CH2:20][N:19]([CH3:18])[CH2:24][CH2:23]4)=[CH:31][CH:30]=3)[N:12]=[CH:13][C:8]=2[CH:7]=[CH:6][C:5]1=[O:17])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 7372534-(4-Methylpiperazin-1-yl)anilineHCID 9989226AluminaHCID 10705897HCID 10705897, compound

Product 1

HCID 5330252HCID 5330252, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
175 °C

Procedure

To 8-isopropyl-2-methanesulfinyl-8H-pyrido[2,3-d]pyrimidin-7-one (212 mg, 0.85 mmol) was added 4-(4-methylpiperazin-1-yl)-aniline (323 mg, 1.69 mmol). The reaction mixture was heated at 175° C. for 10 minutes then cooled to room temperature and partitioned between saturated sodium bicarbonate and chloroform. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified by flash chromatography eluting with 10% methanol in ethyl acetate. The fractions containing product were concentrated, and hexane and ethyl acetate were added to give a solid that was dissolved in chloroform and passed through an aluminum oxide column. The fractions containing product were concentrated, and upon addition of hexane and ethyl acetate, a solid formed providing 160 mg (50%) of 8-isopropyl-2-[4-(4-methylpiperazin-1-yl)-phenylamino]-8H-pyrido[2,3-d]pyrimidin-7-one, mp 221-222° C.

Workup

  1. temperaturethen cooled to room temperature
  2. custompartitioned between saturated sodium bicarbonate and chloroform
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography
  8. washeluting with 10% methanol in ethyl acetate
  9. additionThe fractions containing product
  10. concentrationwere concentrated
  11. additionhexane and ethyl acetate were added
  12. customto give a solid
  13. additionThe fractions containing product
  14. concentrationwere concentrated
  15. additionupon addition of hexane and ethyl acetate
  16. customa solid formed

Sources & evidence

ORD record
ord-72691a4b9e324c0ea359630455c24e3b
Source dataset
uspto-grants-2002_12
Patent number
US06498163B1

Reaction notes

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