1,3,5-Triazine → HCID 13603462, compound

HRID 845762Notes

Reaction equation

HRID 845762 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[C:13]([C:14]([O:16]C)=O)=[C:12]([CH3:18])[NH:11][C:10]([CH3:19])=[C:9]1[C:20]([O:22][CH3:23])=[O:21].[H-].[Na+].[N:26]1C=NC=N[CH:27]=1>CN(C)C=O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[C:13]2[C:14](=[O:16])[NH:26][CH:27]=[CH:18][C:12]=2[NH:11][C:10]([CH3:19])=[C:9]1[C:20]([O:22][CH3:23])=[O:21]

Participants

5

Reactant 3

HCID 92621,3,5-TriazineHCID 24758Sodium hydrideHCID 726139HCID 726139, compound

Product 1

HCID 13603462HCID 13603462, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of 31.5 g (120 mMol) dimethyl 4-(2-fluorophenyl)-1,4-dihydro-2,6-dimethylpyridine-3,5-dicarboxylate in 260 ml dimethylformamide is added dropwise, under an atmosphere of nitrogen, to a suspension of 3.8 g (130 mMol) sodium hydride (80% in paraffin oil) in 60 ml dry dimethylformamide. Upon slowing down of the evolution of gas, the reaction mixture is further stirred for ten minutes at ambient temperature and subsequently 10.0 g (120 mMol) s-triazine in 260 ml dimethylformamide are added dropwise thereto. The reaction mixture is heated to 110° C. for 16 hours and, after cooling, evaporated in a vacuum. The dark residue is stirred with 600 ml acetone, filtered and the filtrate evaporated in a vacuum. The crude product is boiled with 300 ml methanol, the crystals formed after cooling are filtered off and, for further purification, are recrystallized from methanol. There is obtained methyl (±)-4-(2-fluorophenyl)-1,4,5,6-tetrahydro-2-methyl-5-oxo-1,6-naphthyridine-3-carboxylate in the form of pale beige crystals; m.p. 315°-316° C. (decomp.).

Workup

  1. temperatureThe reaction mixture is heated to 110° C. for 16 hours
  2. temperatureafter cooling
  3. customevaporated in a vacuum
  4. stirringThe dark residue is stirred with 600 ml acetone
  5. filtrationfiltered
  6. customthe filtrate evaporated in a vacuum
  7. customthe crystals formed
  8. temperatureafter cooling
  9. filtrationare filtered off and, for further purification
  10. customare recrystallized from methanol

Sources & evidence

ORD record
ord-1647e25c6c0540ab9ea132ccf8ca26b6
Source dataset
uspto-grants-1988_07
Patent number
US04760081

Reaction notes

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