Sodium hydride → (4-Benzyloxy-3,5-dimethyl-phenyl)-(6-chloro-pyrimidin-4-yl)-methanone

HRID 469298

반응식

HRID 469298 반응식
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[N:5]=[CH:4][N:3]=1.[CH2:9]([O:16][C:17]1[C:24]([CH3:25])=[CH:23][C:20]([CH:21]=[O:22])=[CH:19][C:18]=1[CH3:26])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[I-].C[N+]1C2C=CC=CC=2N(C)C=1.[H-].[Na+]>C1COCC1>[CH2:9]([O:16][C:17]1[C:18]([CH3:26])=[CH:19][C:20]([C:21]([C:6]2[CH:7]=[C:2]([Cl:1])[N:3]=[CH:4][N:5]=2)=[O:22])=[CH:23][C:24]=1[CH3:25])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

참가 물질

6

반응물 4

HCID 24758Sodium hydrideHCID 709434,6-DichloropyrimidineHCID 5635574-(Benzyloxy)-3,5-dimethylbenzaldehydeHCID 118217931,3-Dimethyl-1H-benzimidazol-3-ium iodide

생성물 1

HCID 58181140(4-Benzyloxy-3,5-dimethyl-phenyl)-(6-chloro-pyrimidin-4-yl)-methanone

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

150 mg (1.00 mmol) 4,6-dichloropyrimidine, 367 mg (1.50 mmol) 4-benzyloxy-3,5-dimethylbenzaldehyde and 166 mg (0.600 mmol) 1,3-dimethyl-3H-benzimidazol-1-ium-iodide (Chem. Pharm. Bull. 1990, 1147-52) in 10.0 mL THF were stirred at RT. Then 73.0 mg (1.51 mmol) sodium hydride (50% in mineral oil) were added and the reaction mixture was refluxed for 2.5 h. The reaction mixture was added to ice water and extracted with DCM. The organic phase was dried and evaporated down.

후처리

  1. temperaturethe reaction mixture was refluxed for 2.5 h
  2. extractionextracted with DCM
  3. customThe organic phase was dried
  4. customevaporated down

출처 및 근거

ORD 기록
ord-2b99befe98664d19803e34af9b5504b7
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08629137B2

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