Selectfluor → HCID 18662977, compound

HRID 1956179Notes

Reaction equation

HRID 1956179 reaction equation
[CH3:1][C:2]1([CH3:20])[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]1[C:12]1[C:13]([S:18][CH3:19])=[N:14][CH:15]=[N:16][CH:17]=1.[F:21][B-](F)(F)F.F[B-](F)(F)F.ClC[N+]12CC[N+](F)(CC1)CC2>C(#N)C>[CH3:1][C:2]1([CH3:20])[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]1[C:12]1[C:13]([S:18][CH2:19][F:21])=[N:14][CH:15]=[N:16][CH:17]=1

Participants

4

Reactant 2

HCID 2724933SelectfluorHCID 23226990HCID 23226990, compound

Product 1

HCID 18662977HCID 18662977, compoundYield 33.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2.0 g (7.0 mmol) of 5-(2,2-dimethyltetralin-1-yl)-4-methylthiopyrimidine in 100 mL of dry acetonitrile was added with stirring 3.0 g (9.1 mmol) of 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate). The mixture was allowed to react for 16 hours and then most of the acetonitrile was removed by evaporation under reduced pressure. The residue was partitioned between ether and water and the organic phase was recovered, dried over magnesium sulfate, filtered, and concentrated by evaporation under reduced pressure. The residual oil was purified by column chromatography on silica gel to obtain 700 mg of the title compound as a tan solid melting at 126°-128° C.

Workup

  1. customto react for 16 hours
  2. custommost of the acetonitrile was removed by evaporation under reduced pressure
  3. customThe residue was partitioned between ether and water
  4. customthe organic phase was recovered
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated by evaporation under reduced pressure
  8. customThe residual oil was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-9dce83ce0a3748d395cf12d187602d0c
Source dataset
uspto-grants-1998_07
Patent number
US05780465

Reaction notes

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