Acetonitrile → 4-(2-(4-Nitrophenoxy)phenyl)pyrimidin-2-amine

HRID 227807

反応式

HRID 227807 の反応式
CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15][C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=2)O1.C([O-])(=O)C.[K+].Cl[C:32]1[CH:37]=[CH:36][N:35]=[C:34]([NH2:38])[N:33]=1.C(#N)C>C(Cl)Cl.O>[N+:22]([C:19]1[CH:18]=[CH:17][C:16]([O:15][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[C:32]2[CH:37]=[CH:36][N:35]=[C:34]([NH2:38])[N:33]=2)=[CH:21][CH:20]=1)([O-:24])=[O:23]

参加物

7

反応物 4

HCID 6342AcetonitrileHCID 2233322-Amino-4-chloropyrimidineHCID 517044Potassium AcetateHCID 667316814,4,5,5-Tetramethyl-2-(2-(4-nitrophenoxy)phenyl)-1,3,2-dioxaborolane2 回

生成物 1

HCID 667316394-(2-(4-Nitrophenoxy)phenyl)pyrimidin-2-amine

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 6344Dichloromethane溶媒

反応条件

温度
85 °C

実験手順

The compound of step 1 (0.034 g, 0.054 mmol), potassium acetate (0.26 g, 2.7 mmol), 4,4,5,5-tetramethyl-2-(2-(4-nitrophenoxy)phenyl)-1,3,2-dioxaborolane (0.460 g, 1.3 mmol), and 4-chloropyrimidin-2-amine (0.17 g, 1.3 mmol) were combined in a sealed tube under nitrogen, to which 7 nL ACN and water (0.73 ml, 40 mmol) were added. The reaction was sealed and heated to 85° C. overnight. The reaction was diluted with DCM and water, and extracted 2× with DCM. The combined organics were dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The resulting material was purified by silica gel chromatography (MeOH/DCM) to give 4-(2-(4-nitrophenoxy)phenyl)pyrimidin-2-amine as a white solid MS m/z=309 [M+H]+. Calc'd for C16H12N4O3: 308.3.

後処理

  1. additionwere added
  2. customThe reaction was sealed
  3. extractionextracted 2× with DCM
  4. dry with materialThe combined organics were dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting material was purified by silica gel chromatography (MeOH/DCM)

出典と根拠

ORDレコード
ord-925a179aa6d24f6197f6dc0071004c16
出典データセット
uspto-grants-2009_07
特許番号
US07560551B2

関連ノート

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