Ethyl isocyanate → 3-Ethyl-1-(3-nitrophenyl)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione

HRID 1287248Notes

Reaction equation

HRID 1287248 reaction equation
C(O[C:4](=[O:21])[C:5]1[CH:10]=[CH:9][CH:8]=[N:7][C:6]=1[NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=1)C.O1CCCC1.[NH2-].[Na+].[CH2:29]([N:31]=[C:32]=[O:33])[CH3:30]>O>[N+:18]([C:14]1[CH:13]=[C:12]([N:11]2[C:6]3[N:7]=[CH:8][CH:9]=[CH:10][C:5]=3[C:4](=[O:21])[N:31]([CH2:29][CH3:30])[C:32]2=[O:33])[CH:17]=[CH:16][CH:15]=1)([O-:20])=[O:19]

Participants

6

Reactant 4

HCID 8022Ethyl isocyanateHCID 8028TetrahydrofuranHCID 24533Sodium amideHCID 543186632-(m-Nitroanilino)nicotinic acid ethyl ester

Product 1

HCID 127641783-Ethyl-1-(3-nitrophenyl)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dioneYield 54.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 5.7 g of 2-(m-nitroanilino)nicotinic acid ethyl ester and 50 ml of dry tetrahydrofuran was added 1.1 g of sodium amide and the solution was stirred for one hour. To this was added dropwise under cooling 2.9 g of ethyl isocyanate and this mixture was reacted at 60°C for 10 hours. After the reaction was complete, the solvent was distilled off from the mixture, and to the residue obtained was added water to precipitate a crude product. This product was collected by filtration and recrystallized from methanol to give 3.4 g of 1-(m-nitrophenyl)-3-ethylpyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione as colorless needles, melting at 210°-211°C.

Workup

  1. additionTo this was added dropwise
  2. customthis mixture was reacted at 60°C for 10 hours
  3. distillationthe solvent was distilled off from the mixture
  4. customto the residue obtained
  5. customto precipitate a crude product
  6. filtrationThis product was collected by filtration
  7. customrecrystallized from methanol

Sources & evidence

ORD record
ord-270ee2839068435f86c80c9682a1a9b1
Source dataset
uspto-grants-1976_10
Patent number
US03984415

Reaction notes

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