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

HRID 338061
ノート
印刷プレビュー

反応式

HRID 338061 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418397
HCID 178418397、化合物
触媒
HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-97372162171d4e018162bbd48dfd153b
出典データセット
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08889858B2

反応ノート

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