Methyl iodide → 6-[3,5-Bis(trifluoromethyl)benzyl]-4-chloro-5,6,7,8,9,10-hexahydro-10-methyl-2-(methylthio)-5-oxopyrimido[4,5-b][1,5]diazocine

HRID 1829642

반응식

HRID 1829642 반응식
[F:1][C:2]([F:31])([F:30])[C:3]1[CH:4]=[C:5]([CH:23]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:25]=1)[CH2:6][N:7]1[CH2:14][CH2:13][CH2:12][NH:11][C:10]2[N:15]=[C:16]([S:20][CH3:21])[N:17]=[C:18]([Cl:19])[C:9]=2[C:8]1=[O:22].[H-].[Na+].[CH3:34]I>CN(C)C=O.C(OCC)(=O)C>[F:29][C:26]([F:27])([F:28])[C:24]1[CH:23]=[C:5]([CH:4]=[C:3]([C:2]([F:30])([F:1])[F:31])[CH:25]=1)[CH2:6][N:7]1[CH2:14][CH2:13][CH2:12][N:11]([CH3:34])[C:10]2[N:15]=[C:16]([S:20][CH3:21])[N:17]=[C:18]([Cl:19])[C:9]=2[C:8]1=[O:22]

참가 물질

6

반응물 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 220535996-[3,5-Bis(trifluoromethyl)benzyl]-4-chloro-5,6,7,8,9,10-hexahydro-2-(methylthio)-5-oxopyrimido[4,5-b][1,5]diazocine

생성물 1

HCID 220536006-[3,5-Bis(trifluoromethyl)benzyl]-4-chloro-5,6,7,8,9,10-hexahydro-10-methyl-2-(methylthio)-5-oxopyrimido[4,5-b][1,5]diazocine수율 88%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

6-[3,5-bis(trifluoromethyl)benzyl]-4-chloro-5,6,7,8,9,10-hexahydro-2-(methylthio)-5-oxopyrimido[4,5-b][1,5]diazocine(Compound of Reference Example 7; 1.50 g) was dissolved in N,N-dimethylformamide (6 mL). To this solution, sodium hydride (185 mg, 60% oil suspension) was added and the mixture was stirred at room temperature for 1 hour. Methyl iodide (0.4 mL) was then added and the mixture was further stirred at room temperature for 1 hour. The reaction mixture was diluted with ethyl acetate, was sequentially washed with water and a saturated aqueous solution of sodium chloride, and was then dried over anhydrous sodium sulfate. Following removal of the solvent, the residue was purified on a silica gel column-chromatography (ethyl acetate:hexane=1:1) to obtain 6-[3,5-bis(trifluoromethyl)benzyl]-4-chloro-5,6,7,8,9,10-hexahydro-10-methyl-2-(methylthio)-5-oxopyrimido[4,5-b][1,5]diazocine (1.36 g, 88%).

후처리

  1. stirringthe mixture was further stirred at room temperature for 1 hour
  2. washwas sequentially washed with water
  3. dry with materiala saturated aqueous solution of sodium chloride, and was then dried over anhydrous sodium sulfate
  4. customremoval of the solvent
  5. customthe residue was purified on a silica gel column-chromatography (ethyl acetate:hexane=1:1)

출처 및 근거

ORD 기록
ord-6bfc8deeb9894ee9b8e23c9ff6aea477
출처 데이터셋
uspto-grants-2006_06
특허 번호
US07064119B2

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