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Sodium Carbonate → 4-(2-Methyl-6-phenyl[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)benzaldehyde

HRID 503769
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HRID 503769 반응식
Cl[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][N:5]2[N:14]=[C:15]([CH3:17])[N:16]=[C:4]2[N:3]=1.[CH:18]([C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1)=[O:19].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O.ClCCl.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:17][C:15]1[N:16]=[C:4]2[N:3]=[C:2]([C:23]3[CH:24]=[CH:25][C:20]([CH:18]=[O:19])=[CH:21][CH:22]=3)[C:7]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)=[CH:6][N:5]2[N:14]=1
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참가 물질

8

반응물 3

HCID 10340Sodium CarbonateHCID 5910734-Formylphenylboronic AcidHCID 772315025-Chloro-2-methyl-6-phenyl[1,2,4]triazolo[1,5-a]pyrimidine

생성물 1

HCID 866306814-(2-Methyl-6-phenyl[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)benzaldehyde

시약·촉매·용매 4

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
촉매
HCID 962Water용매
HCID 6344Dichloromethane용매
HCID 80711,2-Dimethoxyethane용매

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온도
90 °C

실험 절차

To a mixture of 6.90 g 5-chloro-2-methyl-6-phenyl[1,2,4]triazolo[1,5-a]pyrimidine and 4.65 g 4-formylphenylboronic acid in 100 ml 1,2-dimethoxyethane are added 55 ml of a 10% w/w sodium carbonate solution and 1.03 g dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II). The resulting mixture is heated to 90° C. under an inert gas atmosphere for 18 h. The work up is performed by diluting the reaction mixture with water and dichloromethane, separating the phases and extraction of the aqueous phase with dichloromethane. The combined organic layers are dried over sodium sulphate and the solvent is evaporated. The residue is purified by chromatography on silica gel (dichloromethane/methanol) to yield the desired product.

후처리

  1. customseparating
  2. extractionthe phases and extraction of the aqueous phase with dichloromethane
  3. dry with materialThe combined organic layers are dried over sodium sulphate
  4. customthe solvent is evaporated
  5. customThe residue is purified by chromatography on silica gel (dichloromethane/methanol)

출처 및 근거

ORD 기록
ord-62520672238d43ae8ff1027266bfe380
출처 데이터셋
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07776864B2

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