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(3-Methoxyphenyl)boronic acid → 2-(3-Methoxy-phenyl)-pyrimidine-5-carboxylic acid methyl ester

HRID 2381964
ノート
印刷プレビュー

反応式

HRID 2381964 の反応式
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[N:7][C:8](SC)=[N:9][CH:10]=1)=[O:4].[CH3:13][O:14][C:15]1[CH:16]=[C:17](B(O)O)[CH:18]=[CH:19][CH:20]=1>S1C=CC=C1C([O-])=O.[Cu+].[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[N:7][C:8]([C:19]2[CH:18]=[CH:17][CH:16]=[C:15]([O:14][CH3:13])[CH:20]=2)=[N:9][CH:10]=1)=[O:4]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 2734370(3-Methoxyphenyl)boronic acidHCID 11194721Methyl 2-(Methylthio)pyrimidine-5-carboxylate

生成物 1

HCID 685580872-(3-Methoxy-phenyl)-pyrimidine-5-carboxylic acid methyl ester収率 35.6%

試薬・触媒・溶媒 2

HCID 11194830Cuprous 2-thiophenecarboxylate触媒HCID 11979704Tetrakis(triphenylphosphine)palladium
触媒

反応条件

温度
85 °C

実験手順

2-Methylsulfanyl-pyrimidine-5-carboxylicacid methyl ester (323 mg, 1.75 mmol), Copper(I) thiophene-2-carboxylate (501 mg, 2.63 mmol), tetrakis(triphenylphosphine) palladium(0) (202 mg, 0.175 mmol) and 3-methoxyphenylboronic acid (400 mg, 2.63 mmol) are taken in a glass tube, evacuated, refilled with N2, added anhydrous THF (6 mL) and is heated overnight at 85° C. after closing with a cap. The reaction is cooled to rt, diluted with EtOAc and ammonium hydroxide is added. The organic layer is seperated, dried (MgSO4), filtered and concentrated in vacuo. The residue is purified by flash silica gel chromatography to afford 2-(3-methoxy-phenyl)-pyrimidine-5-carboxylic acid methyl ester (152 mg) as a powder. MS: 245 (M+H); 1H NMR (CDCl3): δ 4.00 (s, 3H), 4.82 (d, 2H), 7.55 (m, 2H), 8.46 (m, 1H), 8.53 (s, 1H), 9.33 (s, 2H).

後処理

  1. customevacuated
  2. additionrefilled with N2
  3. additionadded anhydrous THF (6 mL)
  4. temperatureThe reaction is cooled to rt
  5. additiondiluted with EtOAc and ammonium hydroxide
  6. additionis added
  7. customThe organic layer is seperated
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe residue is purified by flash silica gel chromatography

出典と根拠

ORDレコード
ord-b825e82c44b54f2185f7bf4d56e5402f
出典データセット
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08258130B2

反応ノート

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