2-(Tri-n-butylstannyl)thiophene → HCID 22711977, compound

HRID 352347Notes

Reaction equation

HRID 352347 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:16]=1)[C:7](=[O:15])[C:8]([CH2:12][CH2:13][OH:14])=[C:9]([CH3:11])[N:10]=2.C([Sn](CCCC)(CCCC)[C:22]1[S:23][CH:24]=[CH:25][CH:26]=1)CCC>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CN1CCCC1=O>[OH:14][CH2:13][CH2:12][C:8]1[C:7](=[O:15])[N:6]2[CH:16]=[C:2]([C:22]3[S:23][CH:24]=[CH:25][CH:26]=3)[CH:3]=[CH:4][C:5]2=[N:10][C:9]=1[CH3:11]

Participants

5

Reactant 2

HCID 27793732-(Tri-n-butylstannyl)thiopheneHCID 22711951HCID 22711951, compound

Product 1

HCID 22711977HCID 22711977, compound

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
130 °C

Procedure

In a round-bottom flask under a current of argon, mix 5 g of 7-bromo-3-(2-hydroxyethyl)-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one, 6.2 ml of tributyl-thiophen-2-yl-stannane, 1 g of tetrakis(triphenylphosphine) palladium and 250 ml of N-methylpyrrolidone. Heat the solution at 130° C. for 2 hours and then evaporate off the solvent in vacuo; take up the residue in 200 ml of dichloromethane, wash the solution with 10% potassium fluoride solution, filter, separate off the organic phase and wash it with water. After drying over magnesium sulphate and evaporation, the residue obtained is purified by chromatography on silica gel using a mixture of dichloromethane/methanol: 95/5 as eluant.

Workup

  1. customevaporate off the solvent in vacuo
  2. washwash the solution with 10% potassium fluoride solution
  3. filtrationfilter
  4. customseparate off the organic phase
  5. washwash it with water
  6. dry with materialAfter drying over magnesium sulphate and evaporation
  7. customthe residue obtained
  8. customis purified by chromatography on silica gel using
  9. additiona mixture of dichloromethane/methanol

Sources & evidence

ORD record
ord-78052a060bde4bb0948e77ac98cf46e4
Source dataset
uspto-grants-2004_06
Patent number
US06747032B2

Reaction notes

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