4,6-Dichloro-2-(methylthio)pyrimidine → HCID 86032208, compound

HRID 1786118Notes

Reaction equation

HRID 1786118 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[N:5]=[C:4]([S:9][CH3:10])[N:3]=1.[CH2:11]([Mg]Br)[CH2:12][CH:13]=[CH2:14]>C1COCC1>[CH2:14]([C:6]1[CH:7]=[C:2]([Cl:1])[N:3]=[C:4]([S:9][CH3:10])[N:5]=1)[CH2:13][CH:12]=[CH2:11]

Participants

4

Reactant 2

HCID 805314,6-Dichloro-2-(methylthio)pyrimidineHCID 178418797HCID 178418797, compound

Product 1

HCID 86032208HCID 86032208, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 4,6-dichloro-2-(methylthio)pyrimidine (5.20 g, 26.66 mmol) and tris(acetylacetonate)iron (III) (0.47 g, 1.33 mmol) in THF (130 mL) and DMP (13 mL) at 0° C. was added slowly 3-butenylmagnesium bromide (0.5M in THF, 56 mL, 28.0 mmol). The reaction mixture was stirred overnight. After the reaction was completed, THF was removed by evaporation in vacuo. The residue was dissolved in dichloromethane (100 mL), and washed with water (50 mL×2), dried over MgSO4, filtered and evaporated in vacuo to provide the title compound. MH+215.

Workup

  1. customTHF was removed by evaporation in vacuo
  2. dissolutionThe residue was dissolved in dichloromethane (100 mL)
  3. washwashed with water (50 mL×2)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-dedb3d67986d4c1899d103f65cd94a2e
Source dataset
uspto-grants-2009_03
Patent number
US07507726B2

Reaction notes

Loading…