HCID 20183381, compound → HCID 20183422, compound

HRID 255722Notes

Reaction equation

HRID 255722 reaction equation
[CH3:1][SH:2].CN(C=O)C.Cl[C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=1[C:18]1[C:23]([C:24]([O:26][CH3:27])=[O:25])=[C:22]([CH3:28])[N:21]=[C:20]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[N:19]=1>O1CCCC1>[CH3:28][C:22]1[N:21]=[C:20]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[N:19]=[C:18]([C:10]2[CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=[CH:14][C:9]=2[S:2][CH3:1])[C:23]=1[C:24]([O:26][CH3:27])=[O:25]

Participants

4

Reactant 2

HCID 20183381HCID 20183381, compoundHCID 86741828HCID 86741828, compound

Product 1

HCID 20183422HCID 20183422, compoundYield 12.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl mercaptan-DMF solution (methylmercaptan 66 g/DMF 306 g) (3.8 ml) and methyl 4-(2-chloro-5-nitrophenyl)-6-methyl-2-phenyl-5-pyrimidinecarboxylate (1.5 g) in tetrahydrofuran (25 ml) was added and the mixture was stirred for 3 hours at ambient temperature. The reaction mixture was evaporated in vacuo and the residue was dissolved in a mixture of water (50 ml) and ethyl acetate (100 ml). The organic layer was washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. The solvent was distilled off to give a residue, which was chromatographed on silicagel eluting with a mixture of n-hexane and ethyl acetate (10:1). The fractions containing the desired product were combined and concentrated in vacuo. The crystalline residue was recrystallized from n-hexane to afford methyl 6-methyl-4-(2-methylthio-5-nitrophenyl)-2-phenyl-5-pyrimidinecarboxylate (0.2 g).

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. dissolutionthe residue was dissolved in a mixture of water (50 ml) and ethyl acetate (100 ml)
  3. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. distillationThe solvent was distilled off
  6. customto give a residue, which
  7. customwas chromatographed
  8. washon silicagel eluting with a mixture of n-hexane and ethyl acetate (10:1)
  9. additionThe fractions containing the desired product
  10. concentrationconcentrated in vacuo
  11. customThe crystalline residue was recrystallized from n-hexane

Sources & evidence

ORD record
ord-7ba97d29aadd472e9beb05a69fdfba78
Source dataset
uspto-grants-1987_10
Patent number
US04698340

Reaction notes

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