Sodium Sulfate → HCID 53492724, compound

HRID 2360674Notes

Reaction equation

HRID 2360674 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[S:8][C:9]([C:12]3[N:17]=[C:16]([C:18]4[N:23]=[CH:22][CH:21]=[CH:20][N:19]=4)[CH:15]=[CH:14][CH:13]=3)=[CH:10][N:11]=2)[CH:2]=1.[B-](F)(F)(F)[F:25].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1.S([O-])([O-])(=O)=O.[Na+].[Na+]>C(#N)C>[F:25][C:10]1[N:11]=[C:7]([C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[S:8][C:9]=1[C:12]1[N:17]=[C:16]([C:18]2[N:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 2724933SelectfluorHCID 44598572HCID 44598572, compound

Product 1

HCID 53492724HCID 53492724, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

0.5 g (1.57 mmol) of 2-[6-(2-pyridin-3-ylthiazol-5-yl)pyridin-2-yl]pyrimidine was dissolved in acetonitrile, 1.16 g (3.15 mmol) of 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane ditetrafluoroborate (Selectfluor™) and 1 g (7.04 mmol) of sodium sulphate were added and the mixture was heated at reflux overnight and, after cooling, filtered through Celite. The filtrate was concentrated and purified by chromatography (cyclohexane/ethyl acetate, then ethyl acetate/methanol).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux overnight
  3. temperatureafter cooling
  4. filtrationfiltered through Celite
  5. concentrationThe filtrate was concentrated
  6. custompurified by chromatography (cyclohexane/ethyl acetate

Sources & evidence

ORD record
ord-71c2e2c2430f49498b260bddbc97bdb2
Source dataset
uspto-grants-2014_04
Patent number
US08686156B2

Reaction notes

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