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Allyl bromide → 1-Methyl-3-(1-allyl-2-oxo-6-fluoro-1,2-dihydroquinoline-7-yl)-6-(trifluoromethyl)-pyrimidine-2,4(1H,3H)-dione

HRID 1033163
Notes
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Reaction equation

HRID 1033163 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N:12]1[C:17](=[O:18])[CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[N:14]([CH3:23])[C:13]1=[O:24])[NH:8][C:7](=[O:25])[CH:6]=[CH:5]2.Br[CH2:27][CH:28]=[CH2:29].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:29]([N:8]1[C:9]2[C:4](=[CH:3][C:2]([F:1])=[C:11]([N:12]3[C:17](=[O:18])[CH:16]=[C:15]([C:19]([F:21])([F:22])[F:20])[N:14]([CH3:23])[C:13]3=[O:24])[CH:10]=2)[CH:5]=[CH:6][C:7]1=[O:25])[CH:28]=[CH2:27]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 190253853-(6-Fluoroquinolin-2-on-7-yl)-1-methyl-6-trifluoromethyluracil

Product 1

HCID 190253811-Methyl-3-(1-allyl-2-oxo-6-fluoro-1,2-dihydroquinoline-7-yl)-6-(trifluoromethyl)-pyrimidine-2,4(1H,3H)-dioneYield 75.9%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

These compounds were prepared in a manner analogous to that of Step I of Example 1, using 0.5 gram (0.001 mole) of 3-(6-fluoroquinolin-2-on-7-yl)-1-methyl-6-trifluoromethyluracil (prepared in Step H of Example 1), 0.5 gram (0.003 mole) of 3-bromopropene, and 0.4 gram (0.003 mole) potassium carbonate in 40 mL of N,N-dimethylformamide. The crude reaction product was subjected to column chromatography on silica gel. Elution was accomplished using 1:1 ethyl acetate-heptane and ethyl acetate. The appropriate, product-containing fractions were combined and concentrated under reduced pressure, yielding 0.3 gram of 3-[1-(2-propen-1-yl)-6-fluoroquinolin-2-on-7-yl]-1-methyl-6-trifluoromethyluracil (Compound 26), mp 178°-179° C. Other product-containing fractions were combined and concentrated under reduced pressure, yielding 0.2 gram of the O-alkylated product, 3-[2-(2-propen-1-yloxy)-6-fluoroquinolin-2-on-7-yl]-1-methyl-6-trifluoromethyluracil (Compound 20A). The NMR spectra were consistent with the proposed structures.

Workup

  1. customThese compounds were prepared in a manner analogous to that of Step I of Example 1
  2. customThe crude reaction product
  3. washElution
  4. additionThe appropriate, product-containing fractions
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-eae4816bb0d64ecdab5401a32abe2fb8
Source dataset
uspto-grants-1994_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05310723

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes