Thymine → HCID 54338636, compound

HRID 342538Notes

Reaction equation

HRID 342538 reaction equation
[NH:1]1[CH:9]=[C:7]([CH3:8])[C:5](=[O:6])[NH:4][C:2]1=[O:3].[F:10][C:11]1[CH:16]=[CH:15][C:14](I)=[CH:13][CH:12]=1.CC1C=C(C)C=C(C)N=1>C(Cl)Cl.[Cu-]=O>[F:10][C:11]1[CH:16]=[CH:15][C:14]([N:1]2[CH:9]=[C:7]([CH3:8])[C:5](=[O:6])[NH:4][C:2]2=[O:3])=[CH:13][CH:12]=1.[F:10][C:11]1[CH:16]=[CH:15][C:14]([N:4]2[C:5](=[O:6])[C:7]([CH3:8])=[CH:9][NH:1][C:2]2=[O:3])=[CH:13][CH:12]=1

Participants

7

Reactant 3

HCID 1135ThymineHCID 79532,4,6-TrimethylpyridineHCID 96054-Fluoroiodobenzene

Product 2

HCID 54338636HCID 54338636, compoundHCID 54496861HCID 54496861, compound

Reagents, catalysts & solvents 2

HCID 178419072HCID 178419072, compoundCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of thymine (5 g, 39.6 mmol), 1-fluoro-4-iodobenzene (9.68 g, 5 mL, 43.6 mmol), copper(I) oxide (6.24 g, 43.6 mmol) and 2,4,6-trimethylpyridine (200 mL) was heated 12 hours at reflux with stirring and under an argon atmosphere. The reaction mixture then was cooled to 25° C., diluted with methylene chloride (300 mL), washed with 5% sulfuric acid (5×300 mL) and concentrated. The residue was purified by flash chromatography on silica gel eluting with hexane/ethyl acetate (1:1) to give 1-(4-fluorophenyl)-5-methyl-2,4(1H,3H)-pyrimidinedione (1.85 g, 9.2 mmol), m.p. 212°-214° C., and 3-(4-fluorophenyl)-5-methyl-2,4(1H,3H)-pyrimidinedione (2.39 g, 10.2 mmol), m.p. 229°-231° C.

Workup

  1. temperaturewas heated 12 hours
  2. temperatureat reflux
  3. washwashed with 5% sulfuric acid (5×300 mL)
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography on silica gel eluting with hexane/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-f187344acceb4a97b9ae152cc94a3f28
Source dataset
uspto-grants-1999_01
Patent number
US05859014

Reaction notes

Loading…