Sodium Carbonate → HCID 67315633, compound

HRID 1011871Notes

Reaction equation

HRID 1011871 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH3:9])[N:3]=1.[O:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[CH:12]=[C:11]1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.[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>[O:10]1[C:11]2=[CH:12][CH:13]=[CH:18][C:17]2=[CH:16][CH:15]=[C:14]1[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH3:9])[N:3]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 971134-Chloro-2-methylthiopyrimidineHCID 2776266Benzo[b]furan-2-boronic acid

Product 1

HCID 67315633HCID 67315633, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 312751,4-DioxaneSolvent2×

Procedure

4-Chloro-2-methylthiopyrimidine (1.6 g, 10.0 mmol), 2-benzofuranboronic acid (1.9 g, 12.0 mmol), tetrakis-(triphenylphosphine)-palladium (0.3 g, 0.3 mmol) were dissolved in dioxane (10 ml) and aqueous Na2CO3 (11 ml, 2M solution in water, 22 mmol) was added. The reaction was heated to 80° C. under argon for 16 h after which time the dioxane was evaporated and the reaction mixture diluted with water and extracted with CH2Cl2. The organic was dried (Na2SO4), concentrated and the residue purified by flash column chromatography (CH2Cl2:n-heptane 8:2) to afford the title compound (1.0 g, 43%) as a white solid. MS: 243.0 (MH+).

Workup

  1. customwas evaporated
  2. additionthe reaction mixture diluted with water
  3. extractionextracted with CH2Cl2
  4. dry with materialThe organic was dried (Na2SO4)
  5. concentrationconcentrated
  6. customthe residue purified by flash column chromatography (CH2Cl2:n-heptane 8:2)

Sources & evidence

ORD record
ord-5bf8b17ca0384b76a30012c902107776
Source dataset
uspto-grants-2011_07
Patent number
US07977358B2

Reaction notes

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