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Sodium Carbonate → HCID 58166641、化合物

HRID 626692
ノート
印刷プレビュー

反応式

HRID 626692 の反応式
[NH2:1][C:2]1[CH:7]=[C:6](Cl)[N:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[Na+].[Na+].O1CCO[CH2:17][CH2:16]1>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]>[CH:16]([C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH2:1])[CH:7]=1)=[CH2:17]
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

6

反応物 3

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 2380124-Amino-6-chloropyrimidine

生成物 1

HCID 58166641HCID 58166641、化合物収率 80%

試薬・触媒・溶媒 2

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒
HCID 962
Water
溶媒

反応条件

温度
100 °C

実験手順

A mixture of 4-amino-6-chloropyrimidine (2.5 g, 19.2 mmol), 1,1′-bis(diphenylphosphino)ferrocene palladium dichloride (810 mg, 1.2 mmol), sodium carbonate (8.14 g, 76.8 mmol) and vinyl borane pinacol ester (3.9 mL, 23 mmol) in dioxane (11.5 mL) and water (11.5 mL) under nitrogen, was heated at 100° C. for 20 hours then cooled to ambient temperature. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (0-10% methanol in DCM) to afford the title compound as a yellow solid (1.87 g, 80% yield). 1H NMR (300 MHz, DMSO-d6): δ 8.30 (s, 1H), 6.83 (s, 2H), 6.57 (dd, J=17.2, 10.5 Hz, 1H), 6.36 (s, 1H), 6.26 (dd, J=17.2, 2.1 Hz, 1H), 5.48 (dd, J=10.5, 2.1 Hz, 1H).

後処理

  1. temperaturethen cooled to ambient temperature
  2. customThe reaction mixture was partitioned between ethyl acetate and water
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel flash chromatography (0-10% methanol in DCM)

出典と根拠

ORDレコード
ord-c7e200e202b84383b191c607a4d157fc
出典データセット
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09309240B2

反応ノート

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