Potassium Carbonate → 2-(1-Methyl-3-trifluoromethylpyrazol-5-yl)-4-(1-methyl-3-trifluoromethylpyrazol-5-yloxy)-5-methylpyrimidine

HRID 1859397ノート

反応式

HRID 1859397 の反応式
I[C:2]1[N:7]=[CH:6][C:5]([CH3:8])=[C:4]([O:9][C:10]2[N:14]([CH3:15])[N:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:26][N:27]1[C:31](B(O)O)=[CH:30][C:29]([C:35]([F:38])([F:37])[F:36])=[N:28]1>C1(C)C=CC=CC=1.O.CO.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:26][N:27]1[C:31]([C:2]2[N:3]=[C:4]([O:9][C:10]3[N:14]([CH3:15])[N:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=3)[C:5]([CH3:8])=[CH:6][N:7]=2)=[CH:30][C:29]([C:35]([F:38])([F:37])[F:36])=[N:28]1

参加物

8

反応物 3

HCID 11430Potassium CarbonateHCID 120567122-Iodo-6-(1-methyl-3-trifluoromethylpyrazol-5-yloxy)-5-methylpyrimidineHCID 120567131-Methyl-3-(trifluoroMethyl)pyrazole-5-boronic acid

生成物 1

HCID 102947292-(1-Methyl-3-trifluoromethylpyrazol-5-yl)-4-(1-methyl-3-trifluoromethylpyrazol-5-yloxy)-5-methylpyrimidine

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 887Methanol溶媒HCID 962Water溶媒HCID 1140Toluene溶媒

実験手順

To a solution of 4A (1 g) in toluene (10 ml) is added a 2 M solution of potassium carbonate in water (2.5 ml) under an inert gas atmosphere. A suspension of 4B (0.66 g) and tetrakis(triphenylphosphine)palladium (0.15 g) in methanol (3 ml) is added and the mixture is heated to for 36 h to reflux. After cooling, the organic phase is separated and the water phase is washed twice with ethyl acetate. The combined organic phases are dried, evaporated to dryness and the residue is purified by silica-gel flash chromatography and preparative HPLC. One obtains the title compound as colorless crystals of mp. 113° C.

後処理

  1. additionis added
  2. temperaturethe mixture is heated to for 36 h
  3. temperatureto reflux
  4. temperatureAfter cooling
  5. customthe organic phase is separated
  6. washthe water phase is washed twice with ethyl acetate
  7. customThe combined organic phases are dried
  8. customevaporated to dryness
  9. customthe residue is purified by silica-gel flash chromatography and preparative HPLC

出典と根拠

ORDレコード
ord-c2b9bf2052b244499804956fd1a7ec05
出典データセット
uspto-grants-2003_03
特許番号
US06528456B2

反応ノート

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