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

HRID 733200ノート

反応式

HRID 733200 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

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%.

後処理

  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)

出典と根拠

ORDレコード
ord-0090e022bdd741e3bf693d0ec3078038
出典データセット
uspto-grants-2009_09
特許番号
US07589095B2

反応ノート

読み込み中…