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Cesium carbonate → 5-(2,6-Dichloropyrimidin-4-yl)-3-(trifluoromethyl)pyridin-2-amine

HRID 1778172
ノート
印刷プレビュー

反応式

HRID 1778172 の反応式
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4](Cl)[N:3]=1.CC1(C)C(C)(C)OB([C:18]2[CH:19]=[C:20]([C:25]([F:28])([F:27])[F:26])[C:21]([NH2:24])=[N:22][CH:23]=2)O1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C.O.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[Cl:1][C:2]1[N:3]=[C:4]([C:18]2[CH:19]=[C:20]([C:25]([F:28])([F:27])[F:26])[C:21]([NH2:24])=[N:22][CH:23]=2)[CH:5]=[C:6]([Cl:8])[N:7]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 773782,4,6-TrichloropyrimidineHCID 468641035-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)pyridin-2-amine

生成物 1

HCID 1176780915-(2,6-Dichloropyrimidin-4-yl)-3-(trifluoromethyl)pyridin-2-amine収率 59.3%

試薬・触媒・溶媒 2

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
触媒
HCID 18373917Acetonitrile--water (1/1)溶媒

実験手順

To a microwave vial charged with 2,4,6-trichloropyrimidine (300 mg, 1.64 mmol), 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)pyridin-2-amine (518 mg, 1.80 mmol) and cesium carbonate (1.07 g, 3.27 mmol) in acetonitrile/water (4:1, 30 mL) was added 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride (60 mg, 0.05 mmol) under nitrogen. The mixture was stirred at room temperature for 16 h. The reaction mixture was concentrated in vacuo, and resulting residue was purified by flash column chromatography (15% ethyl acetate in petroleum ether to 50% ethyl acetate in petroleum ether) to provide 5-(2,6-dichloropyrimidin-4-yl)-3-(trifluoromethyl)pyridin-2-amine (300 mg, 59.3% yield). LCMS (ESI): [MH]+=308.7.

後処理

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customresulting residue
  3. customwas purified by flash column chromatography (15% ethyl acetate in petroleum ether to 50% ethyl acetate in petroleum ether)

出典と根拠

ORDレコード
ord-164ab84daca64bfd8381e823dc25c02b
出典データセット
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09266862B2

反応ノート

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