Dimethylformamide → HCID 23020381, compound

HRID 2261028Notes

Reaction equation

HRID 2261028 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH3:9])[N:3]=1.C([Sn](CCCC)(CCCC)[C:15]([O:17][CH2:18][CH3:19])=[CH2:16])CCC.CN(C=O)C.[F-].[K+]>C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(OCC)(=O)C>[CH2:18]([O:17][C:15]([C:2]1[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH3:9])[N:3]=1)=[CH2:16])[CH3:19]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 971134-Chloro-2-methylthiopyrimidineHCID 522689Potassium FluorideHCID 619414Stannane, tributyl(1-ethoxyethenyl)-

Product 1

HCID 23020381HCID 23020381, compoundYield 94.3%

Reagents, catalysts & solvents 2

HCID 178419050HCID 178419050, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture comprising 16.4 g of 4-chloro-2-methylsulfanylpyrimidine, 38 g of tributyl(1-ethoxyvinyl) tin, 1.43 g of bis(triphenylphosphine)palladium (II) dichloride and 100 ml of DMF was stirred at 80° C. for 3 hours. After cooling the reaction mixture, 300 ml of ethyl acetate and 17.8 g of potassium fluoride were added to the mixture, and the resulting mixture was stirred at room temperature overnight. After filtration with Celite, the filtrate was washed, dried and concentrated. The residue was purified by silica gel column chromatography (hexane:ethylacetate=20:1) to give 18.9 g of 4-(1-ethoxy-vinyl)-2-methylsulfanylpyrimidine.

Workup

  1. additionwere added to the mixture
  2. stirringthe resulting mixture was stirred at room temperature overnight
  3. filtrationAfter filtration with Celite
  4. washthe filtrate was washed
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography (hexane:ethylacetate=20:1)

Sources & evidence

ORD record
ord-4412fbb302504dd79355a2e4bfb12edb
Source dataset
uspto-grants-2010_12
Patent number
US07846933B2

Reaction notes

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