2(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl- → HCID 50941330, compound

HRID 1627963Notes

Reaction equation

HRID 1627963 reaction equation
I[C:2]([Si:19]([CH3:22])([CH3:21])[CH3:20])=[C:3]1[C:12](=[C:13](I)[Si:14]([CH3:17])([CH3:16])[CH3:15])[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4]1.C([Li])(C)(C)C.CN1C(=O)N(C)CCC1.I[C:38]1[C:47](I)=[CH:46][C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH:39]=1>C1COCC1.Cl[Cu]>[CH3:20][Si:19]([CH3:22])([CH3:21])[C:2]1[C:47]2[C:38](=[CH:39][C:40]3[C:45]([CH:46]=2)=[CH:44][CH:43]=[CH:42][CH:41]=3)[C:13]([Si:14]([CH3:17])([CH3:16])[CH3:15])=[C:12]2[C:3]=1[CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=1[CH2:11]2

Participants

7

Reactant 4

HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-HCID 10937756HCID 10937756, compoundHCID 75586893HCID 75586893, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 50941330HCID 50941330, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

Compound 2 obtained in step 1 (552 mg, 1.0 mmol) was dissolved in THF (15 ml). To this solution, t-butyllithium (1.76 M in n-pentane, 2.27 mL, 4.0 mmol) was slowly added at −78° C., and this mixture was stirred for 15 minutes. The resulting solution was kept at −40° C. for 30 minutes and then cooled again to −78° C. After 15 minutes passed, this solution was mixed with CuCl (198 mg, 2.0 mmol) and DMPU (0.36 mL, 3.0 mmol), followed by stirring at 0° C. for 0.5 hours. Then, to this reaction mixture, 2,3-diiodonaphthalene (760 mg, 2.0 mmol) was added and heated at 50° C. for 12 hours. The reaction mixture was cooled to 0° C. and then quenched with 3 N HCl, and the reaction product was extracted with hexane. The organic layer was washed with saturated aqueous sodium bicarbonate and aqueous sodium chloride, and then dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (hexane:ethyl acetate:triethylamine=50:1:1) to give the titled compound (compound 3) as a yellow solid (169 mg, yield: 40%).

Workup

  1. waitThe resulting solution was kept at −40° C. for 30 minutes
  2. waitAfter 15 minutes passed
  3. stirringby stirring at 0° C. for 0.5 hours
  4. temperatureheated at 50° C. for 12 hours
  5. temperatureThe reaction mixture was cooled to 0° C.
  6. customquenched with 3 N HCl
  7. extractionthe reaction product was extracted with hexane
  8. washThe organic layer was washed with saturated aqueous sodium bicarbonate and aqueous sodium chloride
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationThe resulting solution was concentrated under reduced pressure
  11. customthe residue was purified by silica gel chromatography (hexane:ethyl acetate:triethylamine=50:1:1)

Sources & evidence

ORD record
ord-ccd028bb221c48d78e1420fb4b0e764b
Source dataset
uspto-grants-2014_07
Patent number
US08785671B2

Reaction notes

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