Methanol → HCID 58203543, compound

HRID 2194741Notes

Reaction equation

HRID 2194741 reaction equation
Cl[C:2]1[N:7]=[C:6](Cl)[C:5]([CH2:9][C:10]([F:13])([F:12])[F:11])=[C:4]([Cl:14])[N:3]=1.[CH3:15][O-:16].[Na+].[CH3:18][OH:19]>>[Cl:14][C:4]1[C:5]([CH2:9][C:10]([F:13])([F:12])[F:11])=[C:6]([O:16][CH3:15])[N:7]=[C:2]([O:19][CH3:18])[N:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 10942334Sodium MethoxideHCID 58203449HCID 58203449, compound

Product 1

HCID 58203543HCID 58203543, compoundYield 90%

Procedure

To a solution of 2,4,6-trichloro-5-(2,2,2-trifluoro-ethyl)-pyrimidine (0.633 g, 2.39 mmol) in methanol (20 mL) at 0° C. was added sodium methoxide (25 wt %, 1.09 mL, 4.77 mmol). The reaction mixture was warmed to room temperature overnight. The reaction mixture was concentrated, dissolved in ethyl ether and washed with water. The organic layer was dried (MgSO4), concentrated and purified by flash column chromatography (silica gel, 0 to 10% ethyl acetate/hexane) to give a colorless oil (0.5531 g, 90%). 1H NMR (300 MHz, CDCl3): δ 3.87 (s, 3H), 3.83 (s, 3H), 3.32 (q, J=10.2 Hz, 2H); Mass spectrum: 257.1, 259.1 (M+H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutiondissolved in ethyl ether
  3. washwashed with water
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated
  6. custompurified by flash column chromatography (silica gel, 0 to 10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-bffef785cb464b1399c6f208140b1a14
Source dataset
uspto-grants-2012_12
Patent number
US08334295B2

Reaction notes

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