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Selectfluor → N-[4-[(1E)-2-[3-(1,1-Dimethylethyl)-5-(5-fluoro-3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl)-2-methoxyphenyl]ethenyl]phenyl]methanesulfonamide

HRID 1924448
Notes
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Reaction equation

HRID 1924448 reaction equation
[C:1]([C:5]1[C:6]([O:32][CH3:33])=[C:7]([CH:21]=[C:22]([N:24]2[CH:29]=[CH:28][C:27](=[O:30])[NH:26][C:25]2=[O:31])[CH:23]=1)/[CH:8]=[CH:9]/[C:10]1[CH:15]=[CH:14][C:13]([NH:16][S:17]([CH3:20])(=[O:19])=[O:18])=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].[B-](F)(F)(F)[F:35].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1>C(#N)C.CO.O>[C:1]([C:5]1[C:6]([O:32][CH3:33])=[C:7]([CH:21]=[C:22]([N:24]2[CH:29]=[C:28]([F:35])[C:27](=[O:30])[NH:26][C:25]2=[O:31])[CH:23]=1)/[CH:8]=[CH:9]/[C:10]1[CH:15]=[CH:14][C:13]([NH:16][S:17]([CH3:20])(=[O:18])=[O:19])=[CH:12][CH:11]=1)([CH3:4])([CH3:2])[CH3:3]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 2724933SelectfluorHCID 57775240Abt-072

Product 1

HCID 25234725N-[4-[(1E)-2-[3-(1,1-Dimethylethyl)-5-(5-fluoro-3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl)-2-methoxyphenyl]ethenyl]phenyl]methanesulfonamideYield 29%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962
Water
Solvent
HCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

The fluorination procedure was performed as described in Lal, G S, et al. J. Org Chem., 60:7340-7342 (1995). The product from Example 13A, Part B (0.42 g, 1.26 mmol) and Selectfluor™ (0.672 g, 1.9 mmol) were combined in a mixture of acetonitrile (8 mL) and methanol (1 mL) and heated at 90° C. under N2 for 5 h. The solution was diluted with water, extracted into ethyl acetate, washed with sodium bicarbonate solution, concentrated and purified by column chromatography on silica gel to give the title compound (0.138 g, 29%).

Workup

  1. extractionextracted into ethyl acetate
  2. washwashed with sodium bicarbonate solution
  3. concentrationconcentrated
  4. custompurified by column chromatography on silica gel

Sources & evidence

ORD record
ord-910de7826eca4e9b835b8d178d9f238d
Source dataset
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08178548B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes