2,6-Dimethylbenzoyl chloride → N'-[1-(2,6-dimethylbenzoyl)-5-fluoro-2-oxo-1,2-dihydro-pyrimidin-4-yl]-N,N-dimethylformamidine

HRID 1260412ノート

反応式

HRID 1260412 の反応式
[F:1][C:2]1[C:3]([N:9]=[CH:10][N:11]([CH3:13])[CH3:12])=[N:4][C:5]([OH:8])=[N:6][CH:7]=1.[CH3:14][C:15]1[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[C:16]=1[C:17](Cl)=[O:18]>N1C=CC=CC=1>[CH3:14][C:15]1[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[C:16]=1[C:17]([N:6]1[CH:7]=[C:2]([F:1])[C:3]([N:9]=[CH:10][N:11]([CH3:13])[CH3:12])=[N:4][C:5]1=[O:8])=[O:18]

参加物

4

反応物 2

HCID 890962,6-Dimethylbenzoyl chlorideHCID 178484257HCID 178484257、化合物

生成物 1

HCID 66954641N'-[1-(2,6-dimethylbenzoyl)-5-fluoro-2-oxo-1,2-dihydro-pyrimidin-4-yl]-N,N-dimethylformamidine収率 37%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
40 °C

実験手順

To an 8 mL screw-cap vial were added pyridine (2 mL), N′-(5-fluoro-2-hydroxy-pyrimidin-4-yl)-N,N-dimethylformamidine (100 mg, 0.54 mmol), and 2,6-dimethylbenzoyl chloride (102 mg, 0.60 mmol). The mixture was heated to 40° C. for 2 h, evaporated to dryness, and partitioned between ethyl acetate (EtOAc) and water (H2O). The organic phase was dried over magnesium sulfate (MgSO4), filtered, evaporated, and the residue was purified by reverse phase chromatography to yield the title compound as a white solid (63 mg, 37%): mp 120-150° C.; 1H NMR (300 MHz, CDCl3) δ 8.81 (s, 1H), 8.22 (d, J=6.04 Hz, 1H), 7.23-7.17 (m, 1H), 7.07-7.01 (m, 2H), 3.27 (s, 3H), 3.24 (s, 3H), 2.24 (s, 6H); ESIMS m/z 317 ([M+H]+).

後処理

  1. customTo an 8 mL screw-cap vial
  2. customevaporated to dryness
  3. custompartitioned between ethyl acetate (EtOAc) and water (H2O)
  4. dry with materialThe organic phase was dried over magnesium sulfate (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customthe residue was purified by reverse phase chromatography

出典と根拠

ORDレコード
ord-8925733bb8854706b102058df8f5f1e6
出典データセット
uspto-grants-2013_06
特許番号
US08470839B2

反応ノート

読み込み中…