Pyrimidine → HCID 20494282, compound

HRID 1075141Notes

Reaction equation

HRID 1075141 reaction equation
[F:1][C:2]1[CH:3]=[N:4][C:5](=[O:8])[NH:6][CH:7]=1.[OH-].[K+].[CH2:11](Br)[CH2:12][OH:13].N1C=CC=NC=1>C(O)C>[OH:13][CH2:12][CH2:11][N:4]1[CH:3]=[C:2]([F:1])[CH:7]=[N:6][C:5]1=[O:8]

Participants

6

Reactant 4

HCID 9260PyrimidineHCID 108982-Bromoethanol2×HCID 14797Potassium Hydroxide2×HCID 1014985-Fluoropyrimidin-2-one

Product 1

HCID 20494282HCID 20494282, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-Fluoropyrimid-2-one (0.008 mol) was dissolved in a solution of potassium hydroxide (0.008 mol) in absolute ethanol (100 ml) at 80° C. and ethylene bromohydrin (0.008 mol) added gradually with stirring. The alkylation was incomplete when the pH had become neutral. The reaction was further monitored by chromatography and equivalent amounts of potassium hydroxide and ethylene bromohydrin added until all the pyrimidine had been alkylated. The reaction mixture was then filtered and the filtrate evaporated to dryness before the residue was triturated with ether and extracted with warm acetone. Evaporation of the acetone solution left the title compound in 50% yield, m.p. 134°-136° C. after recrystallisation from ethanol; Found: C, 45.83; H, 4.42; Calc. for C6H7FN2O2 : C, 45.58; H, 4.46.

Workup

  1. filtrationThe reaction mixture was then filtered
  2. customthe filtrate evaporated to dryness before the residue
  3. customwas triturated with ether
  4. extractionextracted with warm acetone
  5. customEvaporation of the acetone solution
  6. waitleft the title compound in 50% yield, m.p. 134°-136° C.
  7. customafter recrystallisation from ethanol

Sources & evidence

ORD record
ord-dd52ad978929436b89845b0cb535645d
Source dataset
uspto-grants-1983_07
Patent number
US04395406

Reaction notes

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