Dimethylformamide → HCID 12941673, compound

HRID 436403Notes

Reaction equation

HRID 436403 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:8]2[C:13]3[N:14]=[CH:15][CH:16]=[CH:17][C:12]=3[C:11](=[O:18])[NH:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.CN(C)C=O.[H-].[Na+].[CH2:26](I)[CH3:27]>O>[F:1][C:2]1[CH:3]=[C:4]([N:8]2[C:13]3[N:14]=[CH:15][CH:16]=[CH:17][C:12]=3[C:11](=[O:18])[N:10]([CH2:26][CH3:27])[CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 12941663HCID 12941663, compound

Product 1

HCID 12941673HCID 12941673, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2.4 g of 1-(m-fluorophenyl)-4-oxo-1,2,3,4-tetrahydropyrido[2,3-d]pyrimidine and 40 ml of dimethylformamide was added 0.6 g of 50% sodium hydride and the mixture was stirred for one hour at room temperature. To this was further added 4.6 g of ethyl iodide and the resulting mixture was stirred at 60° C for 1.5 hours. After the reaction was finished, the solvent was distilled off from the mixture to leave a residue, to which was added water to precipitate a crude product. Recrystallization of this product from ether gave 2.2 g of 1-(m-fluorophenyl)-3-ethyl-4-oxo-1,2,3,4-tetrahydropyrido[2,3-d]pyrimidine as pale yellow prisms, melting at 123° - 124° C.

Workup

  1. stirringthe resulting mixture was stirred at 60° C for 1.5 hours
  2. distillationthe solvent was distilled off from the mixture
  3. customto leave a residue
  4. customto precipitate a crude product
  5. customRecrystallization of this product from ether

Sources & evidence

ORD record
ord-fa0081cbfe3d469f88cd08c9b892d6d3
Source dataset
uspto-grants-1977_02
Patent number
US04009166

Reaction notes

Loading…