Ammonia → 2-[(E)-2-Phenylethenyl]-5,8-dihydropyrido[2,3-d]pyrimidin-7(1H)-one

HRID 657171Notes

Reaction equation

HRID 657171 reaction equation
Cl[C:2]1[C:7]([CH2:8][CH2:9][C:10](OCC)=[O:11])=[CH:6][N:5]=[C:4](/[CH:15]=[CH:16]/[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:3]=1.[NH3:23].CO>>[C:17]1(/[CH:16]=[CH:15]/[CH:4]2[NH:3][C:2]3[NH:23][C:10](=[O:11])[CH2:9][CH2:8][C:7]=3[CH:6]=[N:5]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 86635376Ethyl 3-{4-chloro-2-[(E)-2-phenylethenyl]-5-pyrimidinyl}propanoate

Product 1

HCID 688170082-[(E)-2-Phenylethenyl]-5,8-dihydropyrido[2,3-d]pyrimidin-7(1H)-oneYield 36.3%

Conditions

Temperature
110 °C

Procedure

To a 320 mL sealed flask at room temperature was added ethyl 3-{4-chloro-2-[(E)-2-phenylethenyl]-5-pyrimidinyl}propanoate (6.6 g, 20.83 mmol) and ammonia in MeOH (59.5 mL, 417 mmol, 7M solution). The flask was sealed and the reaction was heated at 110° C. for 7 h. After 3 h a solid precipitated. The reaction was then stirred at room temperature overnight, followed by heating for an additional 5 h. The reaction mixture was filtered through a Buchner funnel and the resulting solid was washed with ethanol and dried. Obtained solid (2 g, 36.3%). LCMS (ES+) m/z 252 (MH+).

Workup

  1. customTo a 320 mL sealed flask at room temperature
  2. customThe flask was sealed
  3. customAfter 3 h a solid precipitated
  4. temperatureby heating for an additional 5 h
  5. filtrationThe reaction mixture was filtered through a Buchner funnel
  6. washthe resulting solid was washed with ethanol
  7. customdried

Sources & evidence

ORD record
ord-8f6b14aaf6a74322bdfcb647b16388a6
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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