Potassium Fluoride → HCID 19392525, compound

HRID 1755988Notes

Reaction equation

HRID 1755988 reaction equation
Cl[C:2]1[N:7]=[C:6]([O:8][CH2:9][CH3:10])[CH:5]=[CH:4][N:3]=1.[CH2:11]([O:13][C:14]([Sn](CCCC)(CCCC)CCCC)=[CH2:15])[CH3:12].[F-].[K+]>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:14]([O:13][C:11]([C:2]1[N:7]=[C:6]([O:8][CH2:9][CH3:10])[CH:5]=[CH:4][N:3]=1)=[CH2:12])[CH3:15]

Participants

6

Reactant 3

HCID 522689Potassium FluorideHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 47372802-Chloro-4-ethoxypyrimidine

Product 1

HCID 19392525HCID 19392525, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 2-chloro-4-ethoxypyrimidine (6.34 g), (1-ethoxyvinyl)-tri-n-butyltin (14.4 g) and bis(triphenylphosphine)palladium(II) chloride (1 g) in DMF (60 ml) was heated at 90° C. for 60 hours. The reaction mixture was cooled to room temperature and potassium fluoride (100 ml of a 10% aqueous solution) was added. The resulting mixture was stirred for 1 hour then filtered through Hyflo supercel filter aid which was rinsed through with ether. The filtrate was extracted with ether (×2) and the combined extracts were washed with brine, then dried, concentrated and chromatographed using ethyl acetate:hexane 1:4 as the eluant to give 1-ethoxy-1-(4-ethoxypyrimidin-2-yl)-ethylene (2.7 g, 35% yield) as an orange oil; IR maximum (film): 1550cm-1 ; 1H NMR (270 MHz): δ1.40(3H,t), 1.50(3H,t), 4.02(2H,q), 4.45(2H,q), 4.58(1H,d), 5.65(1H,d), 6.60(1 H,d), 8.48(1H,d) ppm.

Workup

  1. filtrationthen filtered through Hyflo supercel
  2. filtrationfilter aid which
  3. washwas rinsed through with ether
  4. extractionThe filtrate was extracted with ether (×2)
  5. washthe combined extracts were washed with brine
  6. customdried
  7. concentrationconcentrated
  8. customchromatographed

Sources & evidence

ORD record
ord-cb053bdc129c421099bc51165779af39
Source dataset
uspto-grants-1995_08
Patent number
US05439910

Reaction notes

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