Potassium Phosphate, Tribasic → 5-Cyclopropyl-2-(2-(2-cyclopropylphenyl)pyrimidin-5-ylamino)benzoic acid

HRID 42062

反応式

HRID 42062 の反応式
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:13]=[CH:12][C:11]([NH:14][C:15]2[CH:23]=[CH:22][C:21]([CH:24]3[CH2:26][CH2:25]3)=[CH:20][C:16]=2[C:17]([OH:19])=[O:18])=[CH:10][N:9]=1.[CH:27]1(B(O)O)[CH2:29][CH2:28]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>C1(C)C=CC=CC=1.O.O>[CH:24]1([C:21]2[CH:22]=[CH:23][C:15]([NH:14][C:11]3[CH:10]=[N:9][C:8]([C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=4[CH:27]4[CH2:29][CH2:28]4)=[N:13][CH:12]=3)=[C:16]([CH:20]=2)[C:17]([OH:19])=[O:18])[CH2:26][CH2:25]1

参加物

7

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acidHCID 569684702-(2-(2-Chlorophenyl)pyrimidin-5-ylamino)-5-cyclopropylbenzoic acid

生成物 1

HCID 251867195-Cyclopropyl-2-(2-(2-cyclopropylphenyl)pyrimidin-5-ylamino)benzoic acid

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 22272177Toluene water溶媒

反応条件

温度
110 °C

実験手順

In a schlenck tube, a mixture of 2-(2-(2-chlorophenyl)pyrimidin-5-ylamino)-5-cyclopropylbenzoic acid (0.55 mmol, 0.200 g), cyclopropylboronic acid (0.71 mmol, 0.061 g), K3PO4 (1.86 mmol, 0.395 g), PCy3 (0.05 mmol, 0.015 g) and Pd(AcO)2 (0.03 mmol, 0.006 g) in a mixture of toluene/water 6:1 (6 ml) was heated at 110° C. for 72 hours, under argon atmosphere. The crude mixture was poured into water and extracted with ethyl acetate. The organic phase was dried over MgSO4, filtered and the solvent removed. The crude mixture was purified by reverse phase chromatography eluting with a gradient of 100% water to 100% MeOH/AcN 1:1 affording 0.016 g (71% of yield).

後処理

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. customthe solvent removed
  5. customThe crude mixture was purified by reverse phase chromatography
  6. washeluting with a gradient of 100% water to 100% MeOH/AcN 1:1 affording 0.016 g (71% of yield)

出典と根拠

ORDレコード
ord-b5c7b4767f8d4872b12910c4e9cdaa0a
出典データセット
uspto-grants-2013_09
特許番号
US08536165B2

関連ノート

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