Tetrahydrofuran → 2-[5-(4-Isobutyl-phenyl)-[1,2,4]oxadiazol-3-yl]-pyrimidine-5-carbaldehyde

HRID 2242216ノート

反応式

HRID 2242216 の反応式
C([Li])CCC.Cl[C:7]1[CH:8]=[N:9][C:10]([C:13]2[N:17]=[C:16]([C:18]3[CH:23]=[CH:22][C:21]([CH2:24][CH:25]([CH3:27])[CH3:26])=[CH:20][CH:19]=3)[O:15][N:14]=2)=[N:11][CH:12]=1.C1C[O:31][CH2:30]C1>CN(C=O)C>[CH2:24]([C:21]1[CH:22]=[CH:23][C:18]([C:16]2[O:15][N:14]=[C:13]([C:10]3[N:9]=[CH:8][C:7]([CH:30]=[O:31])=[CH:12][N:11]=3)[N:17]=2)=[CH:19][CH:20]=1)[CH:25]([CH3:27])[CH3:26]

参加物

5

反応物 3

HCID 8028TetrahydrofuranHCID 592043135-Chloro-2-[5-(4-isobutyl-phenyl)-[1,2,4]oxadiazol-3-yl]-pyrimidineHCID 178418339Butyllithium

生成物 1

HCID 592043082-[5-(4-Isobutyl-phenyl)-[1,2,4]oxadiazol-3-yl]-pyrimidine-5-carbaldehyde収率 76%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

n-Butyllithium (4.77 mL, 7.16 mmol) was added to a solution of 5-chloro-2-[5-(4-isobutyl-phenyl)-[1,2,4]oxadiazol-3-yl]-pyrimidine (1.5 g, 4.77 mmol) and THF (50 mL) at −78° C. and stirred for 7 hours DMF (3 mL) was added to the reaction mixture, warmed to 0° C. and stirred for 2 hours. The reaction mixture was quenched with saturated aqueous ammonium chloride (15 mL) and stirred at room temperature for 12 hours. The reaction mixture was diluted with EtOAc (25 mL) and the organic layer was separated and washed with water (3×25 mL) and brine (1×25 mL) and concentrated in vacuo to provide the title compound (1.13 g, 76% yield) as an orange solid.

後処理

  1. additionwas added to the reaction mixture
  2. customThe reaction mixture was quenched with saturated aqueous ammonium chloride (15 mL)
  3. stirringstirred at room temperature for 12 hours
  4. additionThe reaction mixture was diluted with EtOAc (25 mL)
  5. customthe organic layer was separated
  6. washwashed with water (3×25 mL) and brine (1×25 mL)
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-de8ab14b3d924962abfc769dbb8f72f4
出典データセット
uspto-grants-2010_03
特許番号
US07671043B2

反応ノート

読み込み中…