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

HRID 1091947ノート

反応式

HRID 1091947 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
95 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-4d9a1f3009c4446b9c3cca6a92cb6d61
出典データセット
uspto-grants-2012_03
特許番号
US08129395B2

反応ノート

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