N,N-dimethyl-p-phenylenediamine → C2 Pyrido[2,3-d]pyrimidin-7-one deriv. 31

HRID 2300082Notes

Reaction equation

HRID 2300082 reaction equation
[CH2:1]([N:3]1[C:8]2[N:9]=[C:10](S(C)=O)[N:11]=[CH:12][C:7]=2[CH:6]=[CH:5][C:4]1=[O:16])[CH3:2].[CH3:17][N:18]([CH3:26])[C:19]1[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=1>>[CH3:17][N:18]([CH3:26])[C:19]1[CH:25]=[CH:24][C:22]([NH:23][C:10]2[N:11]=[CH:12][C:7]3[CH:6]=[CH:5][C:4](=[O:16])[N:3]([CH2:1][CH3:2])[C:8]=3[N:9]=2)=[CH:21][CH:20]=1

Participants

3

Reactant 2

HCID 7472N,N-dimethyl-p-phenylenediamineHCID 10752351Pyrido[2,3-d]pyrimidin-7(8H)-one, 8-ethyl-2-(methylsulfinyl)-

Product 1

HCID 5330217C2 Pyrido[2,3-d]pyrimidin-7-one deriv. 31Yield 50%

Conditions

Temperature
175 °C

Procedure

A mixture of 8-ethyl-2-methanesulfinyl-8H-pyrido[2,3-d]pyrimidin-7-one (155 mg, 0.65 mmol) and 500 μL of 4-dimethylaminoaniline was heated at 175° C. for 10 minutes, then cooled to room temperature and partitioned between saturated sodium bicarbonate and ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The resultant solid was washed with hexane and ethyl acetate then purified by flash chromatography eluting with ethyl acetate. The fractions containing product were concentrated and a 2:1 mixture of hexane and ethyl acetate was added to the residue. The resultant precipitate was collected by filtration to give 110 mg (50%) of 2-(4-dimethylamino-phenylamino)-8-ethyl-8H-pyrido[2,3-d]pyrimidin-7-one, mp 189-191° C.

Workup

  1. temperaturecooled to room temperature
  2. custompartitioned between saturated sodium bicarbonate and ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. washThe resultant solid was washed with hexane and ethyl acetate
  8. customthen purified by flash chromatography
  9. washeluting with ethyl acetate
  10. additionThe fractions containing product
  11. concentrationwere concentrated
  12. additiona 2:1 mixture of hexane and ethyl acetate
  13. additionwas added to the residue
  14. filtrationThe resultant precipitate was collected by filtration

Sources & evidence

ORD record
ord-c258c07fe8264c3683bd7a261c76449c
Source dataset
uspto-grants-2002_12
Patent number
US06498163B1

Reaction notes

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