N,N,N',N'-Tetramethylethylenediamine → 4-amino-1-(4-fluoro-phenyl)-1H-pyrimidin-2-one

HRID 538224ノート

反応式

HRID 538224 の反応式
CN(CCN(C)C)C.[NH:9]1[CH:16]=[CH:15][C:13]([NH2:14])=[N:12][C:10]1=[O:11].[F:17][C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1>CO.O.O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[NH2:14][C:13]1[CH:15]=[CH:16][N:9]([C:21]2[CH:22]=[CH:23][C:18]([F:17])=[CH:19][CH:20]=2)[C:10](=[O:11])[N:12]=1

参加物

7

反応物 3

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 2856454-Fluorophenylboronic acidHCID 178418229Cytosine

生成物 1

HCID 682901544-amino-1-(4-fluoro-phenyl)-1H-pyrimidin-2-one収率 321.7%

試薬・触媒・溶媒 3

HCID 165397Cupric acetate monohydrate触媒HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

TMEDA (8 mL, 54 mmol) was added to a stirred suspension of cytosine (3 g, 27 mmol), 4-fluorophenylboronic acid (7.55 g, 5 mmol) and copper(II)acetate monohydrate (5.44 g, 27 mmol) in a mixture of MeOH (960 mL) and H2O (240 mL). The mixture was stirred at RT for 16 hours. The solvents were evaporated in vacuo and the crude product purified by open column chromatography (silica; MeOH in DCM with a gradient of 0/100 to 100/0). The desired fractions were collected and the solvents evaporated in vacuo. The product was triturated with MeOH and DCM and the solid formed filtered and dried in vacuo to yield 4-amino-1-(4-fluoro-phenyl)-1H-pyrimidin-2-one (3.3 g, 60% yield) as a white solid.

後処理

  1. customThe solvents were evaporated in vacuo
  2. customthe crude product purified by open column chromatography (silica
  3. customThe desired fractions were collected
  4. customthe solvents evaporated in vacuo
  5. customThe product was triturated with MeOH and DCM
  6. customthe solid formed
  7. filtrationfiltered
  8. customdried in vacuo

出典と根拠

ORDレコード
ord-06c4d9bb11ff4528a1d71d26c51293e7
出典データセット
uspto-grants-2014_10
特許番号
US08865725B2

反応ノート

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