Methyl iodide → (Rac)-2-chloro-9-cyclobutyl-5,7-dimethyl-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one

HRID 2111379노트

반응식

HRID 2111379 반응식
[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[NH:11][C:10](=[O:12])[CH:9]([CH3:13])[CH2:8][N:7]([CH:14]3[CH2:17][CH2:16][CH2:15]3)[C:6]=2[N:18]=1.I[CH3:20].[H-].[Na+]>CN(C)C=O>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[N:11]([CH3:20])[C:10](=[O:12])[CH:9]([CH3:13])[CH2:8][N:7]([CH:14]3[CH2:17][CH2:16][CH2:15]3)[C:6]=2[N:18]=1

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 87555122HCID 87555122, 화합물

생성물 1

HCID 87618676(Rac)-2-chloro-9-cyclobutyl-5,7-dimethyl-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one수율 89%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a mixture of 0.94 g (0.00352 mole) of (rac)-2-chloro-9-cyclobutyl-7-methyl-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one (VI-52), 0.33 mL (0.00529 mole) of iodomethane and 15 mL of N,N-dimethylformamide at 0 degrees, was added 0.21 g (0.00529 mole) of 60% oil dispersion of sodium hydride. The mixture was stirred at 0 degrees for 2 hours and then partitioned between ethyl acetate and water. The aqueous phase was extracted with ethyl acetate. The combined organic phases were washed successively with water and brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography eluting with hexanes-ethyl acetate (100:0-60:40) to give 0.88 g of (rac)-2-chloro-9-cyclobutyl-5,7-dimethyl-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one (VII-52) as white powder. HRMS (ES+) m/z Calcd for C13H17CLN4O2+H [(M+H)+]: 281.1164. Found: 281.1163.

후처리

  1. custompartitioned between ethyl acetate and water
  2. extractionThe aqueous phase was extracted with ethyl acetate
  3. washThe combined organic phases were washed successively with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography
  8. washeluting with hexanes-ethyl acetate (100:0-60:40)

출처 및 근거

ORD 기록
ord-971888e1a5374e8fbc0aff9857c37312
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07517873B2

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