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

HRID 2242216노트

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HRID 2242216 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-de8ab14b3d924962abfc769dbb8f72f4
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07671043B2

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