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

HRID 2381964
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HRID 2381964 반응식
[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]
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참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 11194830Cuprous 2-thiophenecarboxylate촉매HCID 11979704
Tetrakis(triphenylphosphine)palladium
촉매

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온도
85 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-b825e82c44b54f2185f7bf4d56e5402f
출처 데이터셋
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08258130B2

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