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

HRID 538224노트

반응식

HRID 538224 반응식
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

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 165397Cupric acetate monohydrate촉매HCID 887Methanol용매HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-06c4d9bb11ff4528a1d71d26c51293e7
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08865725B2

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