2-(Methylthio)-5-nitropyridine → HCID 178503249, compound

HRID 1649143Notes

Reaction equation

HRID 1649143 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-])=O)=[CH:5][N:4]=1.O.[Na].Cl[C:15]1[N:20]=[C:19]([OH:21])[C:18]([N+:22]([O-:24])=[O:23])=[CH:17][N:16]=1>C(O)C.[Ni].O>[OH:21][C:19]1[C:18]([N+:22]([O-:24])=[O:23])=[CH:17][N:16]=[C:15]([NH:9][C:6]2[CH:5]=[N:4][C:3]([S:2][CH3:1])=[CH:8][CH:7]=2)[N:20]=1

Participants

7

Reactant 3

HCID 44393132-(Methylthio)-5-nitropyridineHCID 71353970Sodium monohydrateHCID 178526811HCID 178526811, compound

Product 1

HCID 178503249HCID 178503249, compound

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

4.5 gm (0.0264 mol) of 2-methylthio-5-nitro-pyridine were hydrogenated at 50° C. and 5 bars pressure in ethanol in the presence of Raney nickel as the catalyst. After the catalyst had been filtered off and after evaporation of the filtrate in vacuo an oil was obtained. A solution of 6.84 gm (0.032 mol) of the sodium monohydrate salt of 2-chloro-4-hydroxy-5-nitro pyrimidine in 150 ml of water was added to the solution of this oil in water. The aqueous solution was heated for 30 minutes on a steam bath, and the resulting precipitate suction-filtered off, washed with water and dried. 4-Hydroxy-2-(6'-methylmercapto-3-pyridyl)amino-5-nitro-pyrimidine was obtained.

Workup

  1. customwere hydrogenated at 50° C.
  2. filtrationAfter the catalyst had been filtered off
  3. customafter evaporation of the filtrate in vacuo an oil
  4. customwas obtained
  5. temperatureThe aqueous solution was heated for 30 minutes on a steam bath
  6. filtrationthe resulting precipitate suction-filtered off
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-22a7ba523a2e4ba2a0151622d806e013
Source dataset
uspto-grants-1983_11
Patent number
US04415566

Reaction notes

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