Sodium Carbonate → 2-Chloro-4-(2,3,4-trimethoxyphenyl)pyrimidine

HRID 497026ノート

反応式

HRID 497026 の反応式
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[CH3:9][O:10][C:11]1[C:16]([O:17][CH3:18])=[C:15]([O:19][CH3:20])[CH:14]=[CH:13][C:12]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.O>[Cl:1][C:2]1[N:7]=[C:6]([C:12]2[CH:13]=[CH:14][C:15]([O:19][CH3:20])=[C:16]([O:17][CH3:18])[C:11]=2[O:10][CH3:9])[CH:5]=[CH:4][N:3]=1

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 775312,4-DichloropyrimidineHCID 27735822,3,4-Trimethoxybenzeneboronic acid

生成物 1

HCID 223181282-Chloro-4-(2,3,4-trimethoxyphenyl)pyrimidine収率 74.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 1140Toluene溶媒2 回

実験手順

In a 250 mL round-bottomed flask, 1.49 grams (10 mmol) of 2,4-dichloropyrimidine was combined with 2,3,4-trimethoxyphenylboronic acid (2.12 g, 10 mmol), sodium carbonate (2.12 g, 2 equivalents), and 1.15 g (0.1 equivalents) of tetrakis-triphenylphosphinepalladium. Toluene (50 mL) and water (5 mL) were added. The reaction was allowed to reflux under nitrogen overnight. The reaction was diluted with toluene and water and the organic layer was separated, washed with brine, dried (Na2SO4), filtered, and concentrated to afford the crude pyrimidine 5. The compound was purified on silica gel using an eluent of 30% acetone/hexane to afford 2.08 g (74%) of the product 5 as a white solid.

後処理

  1. temperatureto reflux under nitrogen overnight
  2. customthe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto afford the crude pyrimidine 5
  8. customThe compound was purified on silica gel using an eluent of 30% acetone/hexane

出典と根拠

ORDレコード
ord-aa6cd608c38a4c91819a1afb07b5b2b6
出典データセット
uspto-grants-2005_09
特許番号
US06949544B2

反応ノート

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