N-methyl-2-pyrrolidone → 3,6-diethyl-2-phenyl-5-trifluoromethyl-4(3H)-pyrimidinone

HRID 1458

反応式

HRID 1458 の反応式
[CH2:1]([N:3]1[C:8](=[O:9])[C:7](I)=[C:6]([CH2:11][CH3:12])[N:5]=[C:4]1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH3:2].[F:19][C:20]([F:25])([F:24])C([O-])=O.[Na+].CN1CCCC1=O>CCOCC.[Cu]I>[CH2:1]([N:3]1[C:8](=[O:9])[C:7]([C:20]([F:25])([F:24])[F:19])=[C:6]([CH2:11][CH3:12])[N:5]=[C:4]1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH3:2]

参加物

6

反応物 3

HCID 13387N-methyl-2-pyrrolidoneHCID 517019Sodium TrifluoroacetateHCID 196906603,6-diethyl-5-iodo-2-phenyl-4(3H)-pyrimidinone

生成物 1

HCID 196907203,6-diethyl-2-phenyl-5-trifluoromethyl-4(3H)-pyrimidinone収率 42.2%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 3283Diethyl Ether溶媒

実験手順

A mixture of 1.00 g (2.8 mmol) of 3,6-diethyl-5-iodo-2-phenyl-4(3H)-pyrimidinone, 1.08 g (5.7 mmol) of copper (I) iodide, 1.54 g (11.3 mmol) of sodium trifluoroacetate and 8 mL of anhydrous N-methylpyrrolidinone was heated at 175 C for 2 h. The mixture was cooled, diluted with 175 mL of ether, washed with four 50 mL portions of water and dried over MgSO4. Removal of the solvent on the rotovap afforded 0.92 g of crude product as a brown oil. This material was purified by flash chromatography on a 25 g column of silica gel eluting with 100 mL portions of 0, 10, 20, 30, 40, 50 and 75% ether in hexanes to afford 0.35 g of 3,6-diethyl-2-phenyl-5-trifluoromethyl-4(3H)-pyrimidinone (compound 185) as a white solid. 1H-NMR (CDCl3) 1.25(3H,t), 1.30(3H,t), 2.8(2H,q), 4.0(2H,q), 7.5(5H).

後処理

  1. temperaturewas heated at 175 C for 2 h
  2. temperatureThe mixture was cooled
  3. washwashed with four 50 mL portions of water
  4. dry with materialdried over MgSO4
  5. customRemoval of the solvent on the rotovap
  6. customafforded 0.92 g of crude product as a brown oil
  7. customThis material was purified by flash chromatography on a 25 g column of silica gel eluting with 100 mL portions of 0, 10, 20, 30, 40, 50 and 75% ether in hexanes

出典と根拠

ORDレコード
ord-5d84c8f338a741eebe88ed5f50eec903
出典データセット
uspto-grants-1998_03
特許番号
US05726124

関連ノート

読み込み中…