Tetrahydrofuran → HCID 12764185, compound

HRID 1287246Notes

Reaction equation

HRID 1287246 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([N:10]2[C:15]3[N:16]=[CH:17][CH:18]=[CH:19][C:14]=3[C:13](=[O:20])[NH:12][C:11]2=[O:21])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[H-].[Na+].C1(C)C=CC(S(O[CH2:34][C:35]([F:38])([F:37])[F:36])(=O)=O)=CC=1.O1CCCC1>CN(C)C=O.O>[N+:1]([C:4]1[CH:5]=[C:6]([N:10]2[C:15]3[N:16]=[CH:17][CH:18]=[CH:19][C:14]=3[C:13](=[O:20])[N:12]([CH2:34][C:35]([F:38])([F:37])[F:36])[C:11]2=[O:21])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 67942Ethanol, 2,2,2-trifluoro-, 1-(4-methylbenzenesulfonate)HCID 127603011-(m-nitrophenyl)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione

Product 1

HCID 12764185HCID 12764185, compoundYield 88.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2.8 g of 1-(m-nitrophenyl)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione was dissolved in 30 ml of dimethylformamide. To the solution was added 0.6 g of about 50 % sodium hydride and the whole was stirred for 20 minutes at room temperature, and then heated up to 90°C. To this was added dropwise a solution of 7.5 g of 2,2,2-trifluoroethyl p-toluenesulfonate and 20 ml of tetrahydrofuran and the mixture was reacted for 2 hours. After the reaction was complete, the solvent was removed from the resulting mixture by distillation, and to the residue obtained was added water to precipitate a crude product. This product was recrystallized from methanol to yield 3.2 g of 1-(m-nitrophenyl)-3-(2,2,2-trifluoroethyl)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione as pale yellow prisms, melting at 228-229°C.

Workup

  1. temperatureheated up to 90°C
  2. customthe mixture was reacted for 2 hours
  3. customthe solvent was removed from the resulting mixture by distillation
  4. customto the residue obtained
  5. customto precipitate a crude product
  6. customThis product was recrystallized from methanol

Sources & evidence

ORD record
ord-60088e0126d94fdf8fcb6557bca61b0f
Source dataset
uspto-grants-1976_10
Patent number
US03984415

Reaction notes

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