Dimethyl oxalate → HCID 13259319, compound

HRID 436412Notes

Reaction equation

HRID 436412 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13]3[N:14]=[CH:15][CH:16]=[CH:17][C:12]=3[CH2:11][NH:10][C:9]2=[O:18])=[CH:4][CH:3]=1.[H-].[Na+].[H][H].[C:23](OC)(=O)C(OC)=O>O.CN(C)C=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:13]3[N:14]=[CH:15][CH:16]=[CH:17][C:12]=3[CH2:11][N:10]([CH3:23])[C:9]2=[O:18])=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 11120Dimethyl oxalateHCID 24758Sodium hydrideHCID 132593181-(4-Fluorophenyl)-3,4-dihydropyrido[2,3-d]pyrimidin-2(1H)-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 13259319HCID 13259319, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
170 °C

Procedure

To a solution of 2.4 g of 1-(p-fluorophenyl)-2-oxo-1,2,3,4-tetrahydropyrido[2,3-d]pyrimidine and 15 ml of dimethylformamide was added 0.5 g of approximately 50% sodium hydride, and the mixture was allowed to stand until the evolution of hydrogen ceased. To this was further added 5.9 g of dimethyl oxalate and the resulting mixture was heated at 170° C in a sealed-tube for 12 hours. After the reaction was complete, the solvent was removed from the reaction mixture by distillation under reduced pressure. The residue thus obtained was diluted with water, extracted with ether and dehydrated. The ether solution was concentrated and left to give 1.6 g of 1-(p-fluorophenyl)-3-methyl-2-oxo-1,2,3,4-tetrahydropyrido[2,3-d]pyrimidine as colorless needles, melting at 212° - 213° C.

Workup

  1. customthe solvent was removed from the reaction mixture by distillation under reduced pressure
  2. customThe residue thus obtained
  3. extractionextracted with ether
  4. concentrationThe ether solution was concentrated
  5. waitleft

Sources & evidence

ORD record
ord-b6830649fd4d4b69817726be3ab72184
Source dataset
uspto-grants-1977_02
Patent number
US04009166

Reaction notes

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