Potassium Carbonate → 2-(2,6-Diethyl-phenyl)-4-methoxy-6-methyl-pyrimidine-5-carboxylic acid methyl ester

HRID 1455765노트

반응식

HRID 1455765 반응식
[CH3:1][O:2][C:3]([C:5]1[C:6]([O:13][CH3:14])=[N:7][C:8](Cl)=[N:9][C:10]=1[CH3:11])=[O:4].C(=O)([O-])[O-].[K+].[K+].[CH2:21]([C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29][CH3:30])[C:24]=1B(O)O)[CH3:22]>COCCOC.O>[CH3:1][O:2][C:3]([C:5]1[C:6]([O:13][CH3:14])=[N:7][C:8]([C:24]2[C:25]([CH2:29][CH3:30])=[CH:26][CH:27]=[CH:28][C:23]=2[CH2:21][CH3:22])=[N:9][C:10]=1[CH3:11])=[O:4]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 18437832(2,6-Diethylphenyl)boronic acidHCID 575314302-Chloro-4-methoxy-6-methyl-pyrimidine-5-carboxylic acid methyl ester

생성물 1

HCID 575315802-(2,6-Diethyl-phenyl)-4-methoxy-6-methyl-pyrimidine-5-carboxylic acid methyl ester

시약·촉매·용매 2

HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

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온도
95 °C

실험 절차

To a solution of 2-chloro-4-methoxy-6-methyl-pyrimidine-5-carboxylic acid methyl ester (4.1 g, 19.0 mmol) in DME (100 mL) is added potassium carbonate (10.5 g, 76 mmol, 4 eq) in water (40 mL) followed by 2,6-diethylphenylboronic acid (6.77 g, 38 mmol, 2 eq). The resulting mixture is degassed by bubbling with argon for 20 min. Pd(PPh3)4 (5 mol %) is added and the resulting yellow biphasic solution is heated at 95° C. in a sealed tube with magnetic stirring for 18 h. The reaction mixture is cooled to room temperature, diluted with water (100 mL) and extracted with EtOAc (75 mL×3). The combined organic layers are washed with brine (75 mL), dried over magnesium sulfate, filtered and evaporated at reduced pressure. The resulting orange oil is purified by chromatography on silica gel (1:2 ether/hexanes) to afford the title compound as a colorless oil. 1H NMR (CDCl3) δ=7.29 (dd, 1H), 7.14 (d, 2H), 4.00 (s, 3H), 3.98 (s, 3H), 2.55 (s, 3H), 2.39 (q, 4H), 1.10 (t, 6H).

후처리

  1. customThe resulting mixture is degassed
  2. customby bubbling with argon for 20 min
  3. additionPd(PPh3)4 (5 mol %) is added
  4. temperatureThe reaction mixture is cooled to room temperature
  5. additiondiluted with water (100 mL)
  6. extractionextracted with EtOAc (75 mL×3)
  7. washThe combined organic layers are washed with brine (75 mL)
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. customevaporated at reduced pressure
  11. customThe resulting orange oil is purified by chromatography on silica gel (1:2 ether/hexanes)

출처 및 근거

ORD 기록
ord-afca74d933b445a38c0d17f779623017
출처 데이터셋
uspto-grants-2009_01
특허 번호
US07482350B2

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