4-Propyl-6-trimethylstannanyl-pyrimidine-2-carbonitrile → 4-(3-Cyclopentylphenyl)-6-propylpyrimidine-2-carbonitrile

HRID 733200Notes

Reaction equation

HRID 733200 reaction equation
[CH:1]1([C:6]2[CH:11]=[CH:10][CH:9]=[C:8](I)[CH:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:13]([C:16]1[CH:21]=[C:20]([Sn](C)(C)C)[N:19]=[C:18]([C:26]#[N:27])[N:17]=1)[CH2:14][CH3:15]>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH:1]1([C:6]2[CH:7]=[C:8]([C:20]3[CH:21]=[C:16]([CH2:13][CH2:14][CH3:15])[N:17]=[C:18]([C:26]#[N:27])[N:19]=3)[CH:9]=[CH:10][CH:11]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 690493004-Propyl-6-trimethylstannanyl-pyrimidine-2-carbonitrileHCID 690505951-Cyclopentyl-3-iodobenzene

Product 1

HCID 468814494-(3-Cyclopentylphenyl)-6-propylpyrimidine-2-carbonitrileYield 36%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 1-cyclopentyl-3-iodo-benzene (158 mg, 0.58 mmol), 4-propyl-6-trimethylstannanyl-pyrimidine-2-carbonitrile (150 mg, 0.48 mmol) and PdCl2(PPh3)2 (34 mg, 0.05 mmol) in dry DMF (3 ml) was heated to 80° C. for 6 h under a nitrogen atmosphere. More catalyst (40 mg, 0.06 mmol) was added and the mixture was heated for 12 h at 80° C. The solvent was removed under reduced pressure and the residue was partitioned between water (5 ml) and AcOEt (5 ml). The aqueous layer was extracted twice with AcOEt (2×5 ml). The combined organic layers were washed with brine, dried over MgSO4 and concentrated under reduced pressure to give 272 mg of crude product which was purified by silica gel chromatography (eluent:cyclohexane/AcOEt 95/5) to give the above titled compound: 51 mg, yield: 36%, HPLC: 98%.

Workup

  1. temperaturethe mixture was heated for 12 h at 80° C
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was partitioned between water (5 ml) and AcOEt (5 ml)
  4. extractionThe aqueous layer was extracted twice with AcOEt (2×5 ml)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under reduced pressure
  8. customto give 272 mg of crude product which
  9. customwas purified by silica gel chromatography (eluent:cyclohexane/AcOEt 95/5)

Sources & evidence

ORD record
ord-0090e022bdd741e3bf693d0ec3078038
Source dataset
uspto-grants-2009_09
Patent number
US07589095B2

Reaction notes

Loading…