1,8-Diazabicyclo(5.4.0)undec-7-ene → 8-Ethyl-2-phenylamino-8H-pyrido[2,3-d]pyrimidin-7-one

HRID 2300056Notes

Reaction equation

HRID 2300056 reaction equation
[CH2:1]([NH:3][C:4]1[C:9]([CH:10]=[CH:11][C:12](OCC)=[O:13])=[CH:8][N:7]=[C:6]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:5]=1)[CH3:2].N12CCCN=C1CCCCC2>C(N(CC)CC)C>[CH2:1]([N:3]1[C:4]2[N:5]=[C:6]([NH:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:7]=[CH:8][C:9]=2[CH:10]=[CH:11][C:12]1=[O:13])[CH3:2]

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene2×HCID 54014983Ethyl 3-(4-ethylamino-2-phenylamino pyrimidin-5-yl)acrylate

Product 1

HCID 53301998-Ethyl-2-phenylamino-8H-pyrido[2,3-d]pyrimidin-7-one

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a room temperature solution of ethyl 3-(4-ethylamino-2-phenylamino pyrimidin-5-yl)acrylate (179 mg, 0.57mmol) in 10 mL of triethylamine was added 90 μL of 1,8-diazabicyclo[5.4.0]undec-7-ene. The reaction mixture was heated at reflux for 8.5 hours then stirred at room temperature overnight. An additional amount of 1,8-diazabicyclo[5.4.0]undec-7-ene (90 μL) was added, and the reaction mixture was heated at reflux for 9 hours then stirred at room temperature overnight. The reaction mixture was concentrated in vacuo and purified by flash chromatography, followed by recrystallization from ethyl acetate:hexane, to provide 8-ethyl-2-phenylamino-8H-pyrido[2,3-d]pyrimidin-7-one, mp 203-204° C.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 8.5 hours
  3. temperaturethe reaction mixture was heated
  4. temperatureat reflux for 9 hours
  5. stirringthen stirred at room temperature overnight
  6. concentrationThe reaction mixture was concentrated in vacuo
  7. custompurified by flash chromatography
  8. customfollowed by recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-17425cb1dc1f4184b3d29ac750b3a519
Source dataset
uspto-grants-2002_12
Patent number
US06498163B1

Reaction notes

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