Tetrahydrofuran → HCID 59242788, compound

HRID 1514411Notes

Reaction equation

HRID 1514411 reaction equation
I[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH3:9])[N:3]=1.[Br-].[CH3:11][C:12]1[N:17]=[C:16]([Zn+])[CH:15]=[CH:14][CH:13]=1.C1COCC1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1.C(OCC)(=O)C>[CH3:11][C:12]1[N:17]=[C:16]([C:2]2[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH3:9])[N:3]=2)[CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 3

HCID 8028TetrahydrofuranHCID 38589014-Iodo-2-(methylthio)pyrimidineHCID 178426002HCID 178426002, compound

Product 1

HCID 59242788HCID 59242788, compoundYield 90%

Reagents, catalysts & solvents 3

HCID 521585Tris(furan-2-yl)phosphaneCatalystHCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

4-Iodo-2-methylsulfanyl-pyrimidine (1 g, 3.97 mmol) was dissolved in dry and degassed THF (9 ml). Pd(dba)2 (114 mg, 0.20 mmol) and tri(2-furyl)phosphine (50 mg, 0.20 mmol) were added. The mixture was cooled at 0° C. and then a 0.5 M solution of 6-methyl-2-pyridylzinc bromide in THF (13 ml, 6.5 mmol) was slowly added dropwise. After stirring the mixture at room temperature for 3 hours, ethyl acetate was added and the mixture was washed with water. The organic phase was dried (Na2SO4) and evaporated. The residue was purified by flash chromatography DCM-MeOH—NH4OH (20-0.1-0.1) to give 785 mg of the title compound (90% yield).

Workup

  1. customin dry
  2. customdegassed THF (9 ml)
  3. washthe mixture was washed with water
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. customevaporated
  6. customThe residue was purified by flash chromatography DCM-MeOH—NH4OH (20-0.1-0.1)

Sources & evidence

ORD record
ord-d5861096e0704e46b5e7d3aae29edc75
Source dataset
uspto-grants-2012_07
Patent number
US08222266B2

Reaction notes

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