Hydrochloric Acid → HCID 66984909, compound

HRID 1950776Notes

Reaction equation

HRID 1950776 reaction equation
Cl[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([CH3:13])[N:5]=[C:4]([S:14][CH3:15])[N:3]=1.[CH3:16][O:17][C:18]1[CH:19]=[C:20]([CH:22]=[C:23]([O:25][CH3:26])[CH:24]=1)[NH2:21].Cl>C(#N)C.C(OCC)(=O)C.C([O-])(O)=O.[Na+]>[CH3:26][O:25][C:23]1[CH:22]=[C:20]([NH:21][C:2]2[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([CH3:13])[N:5]=[C:4]([S:14][CH3:15])[N:3]=2)[CH:19]=[C:18]([O:17][CH3:16])[CH:24]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 663013,5-DimethoxyanilineHCID 22225416Ethyl 4-chloro-6-methyl-2-(methylsulfanyl)pyrimidine-5-carboxylate

Product 1

HCID 66984909HCID 66984909, compoundYield 72.4%

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A 200 mL RB flask was charged with ethyl 4-chloro-6-methyl-2-(methylthio)pyrimidine-5-carboxylate (2.76 g, 11.1 mmol) in 40 mL acetonitrile. To the solution was added 3,5-dimethoxy aniline (1.784 g, 11.4 mmol), and conc. HCl solution (494 uL, 5.6 mmol), the reaction mixture was stirred at 60˜70° C. for 2 hours. The mixture was diluted with ethyl acetate and saturated aqueous NaHCO3 solution. It was stirred for an additional 5 minutes. The separated organic layer was dried over MgSO4, and condensed under reduced pressure yielding the residue. The residue was recrystallized from acetonitrile, dried under reduced pressure providing pale yellow solids (2.92 g, 72%). MS m/z: 364.1 (M+H)+.

Workup

  1. stirringIt was stirred for an additional 5 minutes
  2. dry with materialThe separated organic layer was dried over MgSO4, and condensed under reduced pressure
  3. customyielding the residue
  4. customThe residue was recrystallized from acetonitrile
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-aa5ec20b622c4f8298cd02e34237f04f
Source dataset
uspto-grants-2013_03
Patent number
US08404677B2

Reaction notes

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