Methanol → 4,6-Difluoro-2-methoxypyrimidine

HRID 1085892Notes

Reaction equation

HRID 1085892 reaction equation
C(N(CC)CC)C.F[C:9]1[N:14]=[C:13]([F:15])[CH:12]=[C:11]([F:16])[N:10]=1.[CH3:17][OH:18]>>[F:16][C:11]1[CH:12]=[C:13]([F:15])[N:14]=[C:9]([O:18][CH3:17])[N:10]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 8471TriethylamineHCID 696772,4,6-Trifluoropyrimidine

Product 1

HCID 139996154,6-Difluoro-2-methoxypyrimidineYield 48%

Conditions

Temperature
25 °C

Procedure

3.8 g (0.0373 mol) of triethylamine were added at -20° C. to a mixture of 5 g (0.0373 mol) of 2,4,6-trifluoropyrimidine in 50 ml of methanol within 5 minutes, and the mixture was stirred at this temperature for a further 40 minutes. After the reaction was complete, the mixture was warmed to 25° C. and the excess methanol was removed by distillation under reduced pressure. The residue obtained in this way was partitioned between methylene chloride and water, and the organic phase was dried over magnesium sulfate and concentrated. 4.6 g (85% of theory) of an isomer mixture which, according to investigation by gas chromatography, contained 46% of the title compound and 48% of 4,6-difluoro-2-methoxypyrimidine were obtained in this way.

Workup

  1. customthe excess methanol was removed by distillation under reduced pressure
  2. customThe residue obtained in this way
  3. customwas partitioned between methylene chloride and water
  4. dry with materialthe organic phase was dried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-72fbf2249ea442b5b22d096d10629db3
Source dataset
uspto-grants-1991_04
Patent number
US05011927

Reaction notes

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