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Sodium Carbonate → 4-Chloro-6-(2-methylpyridin-3-yl)pyrimidine

HRID 2174172
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HRID 2174172 반응식
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.[CH3:9][C:10]1[C:15](B2OC(C)(C)C(C)(C)O2)=[CH:14][CH:13]=[CH:12][N:11]=1.C([O-])(=O)C.[K+].C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(#N)C>[Cl:8][C:6]1[CH:7]=[C:2]([C:15]2[C:10]([CH3:9])=[N:11][CH:12]=[CH:13][CH:14]=2)[N:3]=[CH:4][N:5]=1
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참가 물질

7

반응물 4

HCID 10340Sodium CarbonateHCID 709434,6-DichloropyrimidineHCID 517044Potassium AcetateHCID 164142712-Methylpyridine-3-boronic acid, pinacol ester

생성물 1

HCID 898585944-Chloro-6-(2-methylpyridin-3-yl)pyrimidine수율 24%

시약·촉매·용매 2

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 6342Acetonitrile용매

실험 절차

First, 3.01 g of 4,6-dichloropyrimidine, 10.9 g of 2-methylpyridine-3-boronic acid pinacol ester, 60 mL of 1M aqueous solution of potassium acetate, 60 mL of 1M aqueous solution of sodium carbonate, and 60 mL of acetonitrile were put in a 300 mL three-neck flask, and the air in the flask was replaced with argon. To this mixture, 1.40 g of tetrakis(triphenylphosphine)palladium(0) was added, and the mixture was irradiated with microwaves under conditions of 70° C. and 400 W and for 2 hours to cause a reaction. This reaction mixture was extracted with ethyl acetate, and washing with saturated brine was performed. Anhydrous magnesium sulfate was added to the obtained solution of the extract for drying, and the resulting mixture was gravity-filtered to give a filtrate. A residue obtained by condensing the filtrate was purified by flash column chromatography using ethyl acetate as a developing solvent. A solid obtained by condensing the fraction was purified by flash column chromatography using hexane and ethyl acetate in a ratio of 1:1 as a developing solvent, so that 4-chloro-6-(2-methylpyridin-3-yl)pyrimidine was obtained (a yellow white solid, yield of 24%). A synthetic scheme of Step 1 is shown in (c-1) below.

후처리

  1. customthe mixture was irradiated with microwaves under conditions of 70° C. and 400 W and for 2 hours
  2. customa reaction
  3. extractionThis reaction mixture was extracted with ethyl acetate
  4. washwashing with saturated brine
  5. additionAnhydrous magnesium sulfate was added to the obtained solution of the
  6. extractionextract
  7. customfor drying
  8. filtrationthe resulting mixture was gravity-filtered
  9. customto give a filtrate
  10. customA residue obtained by condensing the filtrate
  11. customwas purified by flash column chromatography
  12. customA solid obtained by condensing the fraction
  13. customwas purified by flash column chromatography

출처 및 근거

ORD 기록
ord-bae732c602fe42d4b1b40e1ee13065e3
출처 데이터셋
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09059414B2

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