Stannous chloride dihydrate → 4,6-Dichloro-2-(methylsulfanyl)pyrimidin-5-amine

HRID 60184

Reaction equation

HRID 60184 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-])=O)=[C:6]([Cl:11])[N:5]=[C:4]([S:12][CH3:13])[N:3]=1.O.O.Cl[Sn]Cl>CCO>[Cl:1][C:2]1[C:7]([NH2:8])=[C:6]([Cl:11])[N:5]=[C:4]([S:12][CH3:13])[N:3]=1

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 113454584,6-Dichloro-2-(methylthio)-5-nitropyrimidine

Product 1

HCID 577424864,6-Dichloro-2-(methylsulfanyl)pyrimidin-5-amineYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 4,6-dichloro-2-methylsulfanyl-5-nitro-pyrimidine (1.0 g, 4.2 mmol) in EtOH (20 mL) was added SnCl2.2H2O (3.8 g, 17 mmol). The mixture was heated to 90° C. After 2 h, the reaction mixture was cooled and the solution was concentrated. The residue was treated with saturated (satd.) aqueous (aq.) NaHCO3 until pH 8. The resulting mixture was then extracted with EtOAc (3×100 mL). The combined organic extracts were dried, filtered, and concentrated. The residue was purified by FCC to afford a colorless solid (723 mg, 87%). MS (ESI): mass calcd. for C5H5Cl2N3S, 208.9; m/z found, 210.3 [M+H]+. 1H NMR ((CD3)2SO): 5.89 (s, 2H), 2.45 (s, 3H).

Workup

  1. temperaturethe reaction mixture was cooled
  2. concentrationthe solution was concentrated
  3. additionThe residue was treated with saturated (satd.) aqueous (aq.) NaHCO3 until pH 8
  4. extractionThe resulting mixture was then extracted with EtOAc (3×100 mL)
  5. customThe combined organic extracts were dried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by FCC

Sources & evidence

ORD record
ord-54919978b75741c2a0c38f1762064981
Source dataset
uspto-grants-2016_09
Patent number
US09440978B2

Linked notes

Loading…