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

HRID 497026노트

반응식

HRID 497026 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매2회HCID 1140Toluene용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-aa6cd608c38a4c91819a1afb07b5b2b6
출처 데이터셋
uspto-grants-2005_09
특허 번호
US06949544B2

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