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

HRID 733200노트

반응식

HRID 733200 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

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%.

후처리

  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)

출처 및 근거

ORD 기록
ord-0090e022bdd741e3bf693d0ec3078038
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07589095B2

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