Potassium Carbonate → methyl 4-(2,5-dimethylpyrimidin-4-yl)-1-methyl-1H-pyrazole-5-carboxylate

HRID 60136

反応式

HRID 60136 の反応式
CC1(C)C(C)(C)OBO1.Br[C:11]1[CH:12]=[N:13][N:14]([CH3:20])[C:15]=1[C:16]([O:18][CH3:19])=[O:17].C(=O)([O-])[O-].[K+].[K+].Cl[C:28]1[C:33]([CH3:34])=[CH:32][N:31]=[C:30]([CH3:35])[N:29]=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.O.O1CCOCC1.C(N(CC)CC)C>[CH3:35][C:30]1[N:31]=[C:32]([C:11]2[CH:12]=[N:13][N:14]([CH3:20])[C:15]=2[C:16]([O:18][CH3:19])=[O:17])[C:33]([CH3:34])=[CH:28][N:29]=1

参加物

10

反応物 4

HCID 11430Potassium CarbonateHCID 673643Methyl 4-bromo-1-methyl-1H-pyrazole-5-carboxylateHCID 27347684,4,5,5-Tetramethyl[1,3,2]dioxaborolane2 回HCID 124653814-Chloro-2,5-dimethylpyrimidine

生成物 1

HCID 90383435methyl 4-(2,5-dimethylpyrimidin-4-yl)-1-methyl-1H-pyrazole-5-carboxylate収率 110%

試薬・触媒・溶媒 5

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl触媒HCID 962Water溶媒HCID 8471Triethylamine溶媒HCID 312751,4-Dioxane溶媒2 回

反応条件

温度
100 °C

実験手順

4,4,5,5-Tetramethyl-1,3,2-dioxaborolane (1.5 ml) was added to a 1,4-dioxane (19 ml) solution of methyl 4-bromo-1-methyl-1H-pyrazole-5-carboxylate (1.9 g), 2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl (0.15 g), Tris(dibenzylideneacetone)dipalladium(0) (0.16 g), and triethylamine (3.7 ml). The obtained mixture was stirred in a nitrogen atmosphere at 100° C. for 30 minutes. Thereafter, 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.5 ml) was added to the reaction solution, and the obtained mixture was then stirred for 30 minutes at the same temperature as described above. Thereafter, an aqueous solution (3.9 ml) of potassium carbonate (3.6 g) and a 1,4-dioxane (4 ml) solution of 4-chloro-2,5-dimethylpyrimidine (1.0 g) were successively added to the reaction solution, and the obtained mixture was then stirred at the same temperature as described above for 1 hour. Thereafter, water was added to the reaction solution, and the mixed solution was extracted with ethyl acetate and was then dried over anhydrous sodium sulfate. The solvent was distilled away under reduced pressure, and the obtained residue was purified by silica gel column chromatography (silica gel:eluent; heptane:ethyl acetate=3:1-1:1-0:1), so as to obtain the title compound (1.9 g) in the form of an orange liquid.

後処理

  1. stirringthe obtained mixture was then stirred for 30 minutes at the same temperature
  2. stirringthe obtained mixture was then stirred at the same temperature
  3. customas described above for 1 hour
  4. extractionthe mixed solution was extracted with ethyl acetate
  5. dry with materialwas then dried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled away under reduced pressure
  7. customthe obtained residue was purified by silica gel column chromatography (silica gel:eluent; heptane:ethyl acetate=3:1-1:1-0:1)

出典と根拠

ORDレコード
ord-703c64c185294d3fb38394e58541bf0b
出典データセット
uspto-grants-2016_09
特許番号
US09440970B2

関連ノート

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