Ethyl 4-(2-chloro-5-nitrophenyl)-6-methyl-2-phenyl-5-pyrimidinecarboxylate → Ethyl 6-methyl-4-(2-methylthio-5-nitrophenyl)-2-phenyl-5-pyrimidinecarboxylate

HRID 255713Notes

Reaction equation

HRID 255713 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11]1[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:15]([CH3:22])[N:14]=[C:13]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:12]=1.[CH3:29][SH:30].[Na]>O1CCCC1>[CH3:22][C:15]1[N:14]=[C:13]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:12]=[C:11]([C:3]2[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=2[S:30][CH3:29])[C:16]=1[C:17]([O:19][CH2:20][CH3:21])=[O:18]

Participants

4

Reactant 2

HCID 15147503Ethyl 4-(2-chloro-5-nitrophenyl)-6-methyl-2-phenyl-5-pyrimidinecarboxylateHCID 45051789Methylmercaptan sodium

Product 1

HCID 15147504Ethyl 6-methyl-4-(2-methylthio-5-nitrophenyl)-2-phenyl-5-pyrimidinecarboxylateYield 19.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tetrahydrofuran (25 ml), methylmercaptan-diemthylformamide solution (methylmercaptan 66 g/DMF 306 g) (5 ml) and ethyl 4-(2-chloro-5-nitrophenyl)-6-methyl-2-phenyl-5-pyrimidinecarboxylate (2 g), sodium methylmercaptan (0.42 g) was added, stirred for 3 h 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. The residue was chromatographed on silica gel, eluting with a mixture of n-hexane and ethyl acetate (10:1). The fractions containing the object compound were combined and concentrated in vacuo. The crystalline residue was recrystallized from diethyl ether to afford ethyl 6-methyl-4-(2-methylthio-5-nitrophenyl)-2-phenyl-5-pyrimidinecarboxylate (0.4 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. customThe residue was chromatographed on silica gel
  7. washeluting with a mixture of n-hexane and ethyl acetate (10:1)
  8. additionThe fractions containing the object compound
  9. concentrationconcentrated in vacuo
  10. customThe crystalline residue was recrystallized from diethyl ether

Sources & evidence

ORD record
ord-2b657d10e6a1446299190095aeef4968
Source dataset
uspto-grants-1987_10
Patent number
US04698340

Reaction notes

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