Dimethyl Sulfate → HCID 13236747, compound

HRID 436404Notes

Reaction equation

HRID 436404 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][CH2:11]2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[H-].[Na+].S(OC)(O[CH3:27])(=O)=O.C(=O)([O-])[O-].[Na+].[Na+]>O.CN(C)C=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]([CH3:27])[CH2:11]2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 6497Dimethyl SulfateHCID 10340Sodium CarbonateHCID 24758Sodium hydrideHCID 12941669HCID 12941669, compound

Product 1

HCID 13236747HCID 13236747, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2.7 g of 1-(m-nitrophenyl)-4-oxo-1,2,3,4-tetrahydropyrido[2,3-d]pyrimidine and 20 ml of dry dimethylformamide was added 0.48 g of approximately 55% sodium hydride and the mixture was stirred at room temperature for 30 minutes. To this was added dropwise 2.52 g of dimethyl sulfate and the whole was stirred at room temperature for 3 hours. The reaction mixture was neutralized with sodium carbonate and concentrated under reduced pressure to leave a residue, to which was added water to precipitate a crude product. This product was collected by filtration and recrystallized from a mixture of dimethylformamide and methanol to give 1.96 g of 1-(m-nitrophenyl)-3-methyl-4-oxo-1,2,3,4-tetrahydropyrido[2,3-d]pyrimidine as yellow needles, melting at 247° - 248° C.

Workup

  1. stirringthe whole was stirred at room temperature for 3 hours
  2. concentrationconcentrated under reduced pressure
  3. customto leave a residue
  4. customto precipitate a crude product
  5. filtrationThis product was collected by filtration
  6. customrecrystallized from a mixture of dimethylformamide and methanol

Sources & evidence

ORD record
ord-66639a995ade4bdabc973d298e1ec517
Source dataset
uspto-grants-1977_02
Patent number
US04009166

Reaction notes

Loading…