Triethylamine → HCID 18315068, compound

HRID 1421458Notes

Reaction equation

HRID 1421458 reaction equation
[CH3:1][N:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5](=[O:12])[N:4]([C:13]2[C:18]([NH2:19])=[C:17]([OH:20])[C:16]([Br:21])=[CH:15][C:14]=2[F:22])[C:3]1=[O:23].[C:24]([O:27][C:28]([C:31](Cl)=O)([CH3:30])[CH3:29])(=[O:26])[CH3:25].C(N(CC)CC)C.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C1(C)C(C)=CC=CC=1.C(OCC)(=O)C>[CH3:1][N:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5](=[O:12])[N:4]([C:13]2[C:18]3[N:19]=[C:29]([C:28]([O:27][C:24]([CH3:25])=[O:26])([CH3:31])[CH3:30])[O:20][C:17]=3[C:16]([Br:21])=[CH:15][C:14]=2[F:22])[C:3]1=[O:23]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 1234962-Acetoxyisobutyroyl chlorideHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 18315063HCID 18315063, compound

Product 1

HCID 18315068HCID 18315068, compoundYield 109%

Reagents, catalysts & solvents 2

HCID 7237O-XyleneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A stirred solution of 0.50 gram (0.0013 mole) of 1-methyl-6-trifluoromethyl-3-(6-amino-4-bromo-2-fluoro-5-hydroxyphenyl)-2,4(1H,3H)-pyrimidinedione, 0.21 gram (0.0013 mole) of 1-chlorocarbonyl-1-methylethyl acetate, 0.14 gram (0.0014 mole) of triethylamine, and 0.16 gram (0.0006 mole) of pyridinium p-toluenesulfonate in 50 mL of xylene was heated at 150 ° C. for about 18 hours. The reaction mixture was then cooled to ambient temperature and taken up in ethyl acetate. The solution was washed with water and an aqueous solution saturated with sodium chloride; then it was dried with magnesium sulfate. The mixture was filtered, and the filtrate was concentrated under reduced pressure to a residue. The residue was purified by column chromatography on silica gel, yielding 0.72 gram of Compound 104. The NMR spectrum was consistent with the proposed structure.

Workup

  1. washThe solution was washed with water
  2. dry with materialthen it was dried with magnesium sulfate
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure to a residue
  5. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-c8b79b7338864d708f528a537596faff
Source dataset
uspto-grants-2000_06
Patent number
US06077812

Reaction notes

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