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2-Chloro-4,6-dimethoxy-5-nitropyrimidine → 2-(4-Fluoro-benzyl)-4,6-dimethoxy-5-nitro-pyrimidine

HRID 334998
ノート
印刷プレビュー

反応式

HRID 334998 の反応式
Cl[C:2]1[N:7]=[C:6]([O:8][CH3:9])[C:5]([N+:10]([O-:12])=[O:11])=[C:4]([O:13][CH3:14])[N:3]=1.[Cl-].[F:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21][Zn+])=[CH:19][CH:18]=1>C1COCC1.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>[F:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21][C:2]2[N:7]=[C:6]([O:8][CH3:9])[C:5]([N+:10]([O-:12])=[O:11])=[C:4]([O:13][CH3:14])[N:3]=2)=[CH:19][CH:18]=1
参加物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 109985372-Chloro-4,6-dimethoxy-5-nitropyrimidineHCID 178505764HCID 178505764、化合物

生成物 1

HCID 576951302-(4-Fluoro-benzyl)-4,6-dimethoxy-5-nitro-pyrimidine収率 68.2%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 8028Tetrahydrofuran溶媒

実験手順

(26) A solution of compound (25) (1.2 g, 5.5 mmol), 4-fluorobenzylzinc chloride (13.1 mL, 0.5 M in THF, 6.6 mmol), tetrakis(triphenylphosphine)palladium (0.13 g, 0.1 mmol) in THF (50 mL) was heated to refluxed for 3 hours under nitrogen. After it cooled to room temperature, the THF was removed in vacuo. The residue was diluted with ethyl acetate, washed with water and brine, dried over Na2SO4. After concentrated, the residue was purified by a column chromatography on silica gel eluting with 5% ethyl acetate in hexane to yield 2-(4-fluoro-benzyl)-4,6-dimethoxy-5-nitro-pyrimidine (26) (1.1 g, 63%). 1H NMR (CDCl3)

後処理

  1. temperatureto refluxed for 3 hours under nitrogen
  2. customthe THF was removed in vacuo
  3. additionThe residue was diluted with ethyl acetate
  4. washwashed with water and brine
  5. dry with materialdried over Na2SO4
  6. concentrationAfter concentrated
  7. customthe residue was purified by a column chromatography on silica gel eluting with 5% ethyl acetate in hexane

出典と根拠

ORDレコード
ord-992b50dee6734a169c3ec7f10fa27b8c
出典データセット
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08883833B2

反応ノート

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