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Potassium Phosphate, Tribasic → HCID 117940279、化合物

HRID 1482167
ノート
印刷プレビュー

反応式

HRID 1482167 の反応式
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]=[CH:4][N:3]=1.[C:14]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1B(O)O)([CH3:17])([CH3:16])[CH3:15].P([O-])([O-])([O-])=O.[K+].[K+].[K+].COC1C=CC=C(OC)C=1P(C1C(OC)=CC=CC=1OC)C1C(OC)=CC=CC=1OC.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C1(C)C=CC=CC=1>[C:14]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]=[CH:4][N:3]=1)([CH3:17])([CH3:16])[CH3:15]
参加物実験手順後処理出典と根拠反応ノート

参加物

11

反応物 5

HCID 62657Potassium Phosphate, Tribasic2 回HCID 5934294-Chloro-6-phenylpyrimidineHCID 2734597Tris(2,6-dimethoxyphenyl)phosphine2 回HCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl3 回HCID 22173077(2-Tert-butylphenyl)boronic acid2 回

生成物 1

HCID 117940279
HCID 117940279、化合物
収率 18%

試薬・触媒・溶媒 5

HCID 167845palladium(II) acetate触媒3 回HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium触媒HCID 9811564Bis(dibenzylideneacetone)palladium触媒2 回HCID 962Water溶媒HCID 1140Toluene溶媒

実験手順

First, 1.0 g of 4-chloro-6-phenylpyrimidine, 1.1 g of 2-tert-butylphenylboronic acid, 4.0 g of potassium phosphate, 39 mL of toluene, and 3.9 mL of water were put in a three-neck flask equipped with a reflux pipe, and the air in the flask was replaced with nitrogen. In this container were added 48 mg of bis(dibenzylideneacetone)palladium(0), namely Pd2(dba)3, and 190 mg of tris(2,6-dimethoxyphenyl)phosphine, and heating was performed at 100° C. for 7 hours. Then, 24 mg of Pd2(dba)3 and 46 mg of tris(2,6-dimethoxyphenyl)phosphine were added and heating was performed at 100° C. for 17 hours. After that, 12 mg of palladium acetate and 44 mg of 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (abbreviation: S-Phos) were added and heating was performed at 100° C. for 15 hours. Furthermore, 5.9 mg of palladium acetate and 27 mg of S-Phos (abbreviation) were added and heating was performed at 100° C. for 8 hours. Then, 0.10 g of 2-tert-butylphenylboronic acid, 2.0 g of potassium phosphate, 13 mg of palladium acetate, and 12 mg of S-Phos (abbreviation) were added and heating was performed at 100° C. for 21 hours. An organic layer was extracted from the obtained mixture with the use of ethyl acetate and was washed with saturated brine. Magnesium sulfate was added and the mixture was subjected to filtration. The solvent in the filtrate was distilled off to give a residue. The residue was purified by neutral silica gel column chromatography using a mixed solvent of ethyl acetate and hexane in a ratio of 1:4 as a developing solvent, so that 0.27 g of Hppm-tBup (abbreviation) that is an objective substance was obtained as a yellowish white solid in a yield of 18%. A synthesis scheme of Step 1 is shown in (b-1) below.

後処理

  1. customequipped with a reflux pipe
  2. temperatureheating
  3. temperatureheating
  4. waitwas performed at 100° C. for 17 hours
  5. temperatureheating
  6. waitwas performed at 100° C. for 15 hours
  7. temperatureheating
  8. waitwas performed at 100° C. for 8 hours
  9. temperatureheating
  10. waitwas performed at 100° C. for 21 hours
  11. extractionAn organic layer was extracted from the obtained mixture with the use of ethyl acetate
  12. washwas washed with saturated brine
  13. additionMagnesium sulfate was added
  14. filtrationthe mixture was subjected to filtration
  15. distillationThe solvent in the filtrate was distilled off
  16. customto give a residue
  17. customThe residue was purified by neutral silica gel column chromatography
  18. customwas obtained as a yellowish white solid in a yield of 18%
  19. customA synthesis scheme of Step 1

出典と根拠

ORDレコード
ord-bbcdda368ef64a5f822eb32efd232ea5
出典データセット
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09412956B2

反応ノート

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このページの内容参加物実験手順後処理出典と根拠反応ノート