5-Fluoropyrimidin-2-one → HCID 12791247, compound

HRID 1906152Notes

Reaction equation

HRID 1906152 reaction equation
[F:1][C:2]1[CH:3]=[N:4][C:5](=[O:8])[NH:6][CH:7]=1.Br[CH2:10][C:11]([C:13]1[S:14][CH:15]=[CH:16][CH:17]=1)=[O:12]>C(N(CC)CC)C.C(O)C>[F:1][C:2]1[CH:3]=[N:4][C:5](=[O:8])[N:6]([CH2:10][C:11](=[O:12])[C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)[CH:7]=1

Participants

5

Reactant 2

HCID 1014985-Fluoropyrimidin-2-oneHCID 27763722-Bromo-1-(thiophen-2-yl)ethan-1-one

Product 1

HCID 12791247HCID 12791247, compoundYield 23.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 5-fluoropyrimidin-2-one (456 mg) and 2-bromoacetylthiophene (820 mg) in triethylamine (1.33 ml) and ethanol (25 ml) was stirred at room temperature. After 2.5 h. the reaction mixture was concentrated to ca. 5 ml, diluted with ethyl acetate (300 ml) washed with water (3×50 ml), dried (MgSO4) and evaporated to a foam. This was crystallised from acetone to give the title pyrimidinone (225 mg), m.p. 183°-190° C. (dec) λmax (EtOH) 260 nm (ε10,308), 285.5 nm (ε 8,430).

Workup

  1. concentrationAfter 2.5 h. the reaction mixture was concentrated to ca. 5 ml
  2. additiondiluted with ethyl acetate (300 ml)
  3. washwashed with water (3×50 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated to a foam
  6. customThis was crystallised from acetone

Sources & evidence

ORD record
ord-bd65b806e6724cc5a66bb2f1160cc420
Source dataset
uspto-grants-1987_03
Patent number
US04650800

Reaction notes

Loading…