Ethyl Acetate → 4-Chloro-6-methylsulfanylpyrimidin-2-amine

HRID 2367177Notes

Reaction equation

HRID 2367177 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[N:5]=[C:4]([NH2:9])[N:3]=1.[CH3:10][S-:11].[Na+].CCOC(C)=O>CCO>[Cl:1][C:2]1[CH:7]=[C:6]([S:11][CH3:10])[N:5]=[C:4]([NH2:9])[N:3]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 655222-Amino-4,6-dichloropyrimidineHCID 4378561Sodium methanethiolate

Product 1

HCID 2376264-Chloro-6-methylsulfanylpyrimidin-2-amineYield 84.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 4,6-dichloro-2-pyrimidinamine (1.0 g, 6.1 mmol) in EtOH (15 ml) was added sodium thiomethoxide (0.43 g, 6.10 mmol) and the reaction mixture was stirred for 1 hour at room temperature. The mixture was poured onto water and EtOAc. The organic layer was separated and the aqueous layer was further extracted with EtOAc. The combined organic layers were washed with brine, dried (MgSO4), filtered and concentrated to afford the crude title compound (910 mg) as a yellow solid. LC-MS (ES) m/z=176 [M+H]+.

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was further extracted with EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-62111cd67a7a44b896df858ff7190ae8
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

Loading…