Bromopinacolone → 5-Ethoxycarbonyl-2-methyl-3-(2-oxo-3,3-dimethyl-butyl)pyrimid-4-one

HRID 1862218

반응식

HRID 1862218 반응식
[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:13])[NH:8][C:9]([CH3:12])=[N:10][CH:11]=1)=[O:5])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.Br[CH2:33][C:34](=[O:39])[C:35]([CH3:38])([CH3:37])[CH3:36]>COCCOC>[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:13])[N:8]([CH2:33][C:34](=[O:39])[C:35]([CH3:38])([CH3:37])[CH3:36])[C:9]([CH3:12])=[N:10][CH:11]=1)=[O:5])[CH3:2]

참가 물질

5

반응물 3

HCID 21642BromopinacoloneHCID 293750Ethyl 4-hydroxy-2-methylpyrimidine-5-carboxylateHCID 2724141Tetrabutylammonium Fluoride

생성물 1

HCID 186196935-Ethoxycarbonyl-2-methyl-3-(2-oxo-3,3-dimethyl-butyl)pyrimid-4-one

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매

실험 절차

To a suspension of 5-ethoxycarbonyl-2-methylpyrimid-4-one (2.7 g, 14.75 mmol.) in DME (20 ml), tetrabutylammonium fluoride (22 ml, 22.0 mmol.) was added. The solution was stirred at room temperature until solids dissolved, then 1-bromopinacolone (2.2 ml, 1.1 eq., 16.22 mmol) was added. The solution was stirred overnight and concentrated to a brown oil. The crude mixture was purified by silica gel column chromatography (hexane/ethyl acetate, 100/0 to 0/100). A less polar O-alkylated by-product was eluted first (1.8 g) and then the desired N-alkylated product (1.1 g); MS (281, M+H)+. NMR (CDCl3, δ): 8.57 (1H, s) , 5.06(1H, s), 4.35(2H, q), 2.42 (3H, s), 1.34 (3H, t), 1.30 (9H,s).

후처리

  1. additionwas added
  2. dissolutiondissolved
  3. stirringThe solution was stirred overnight
  4. concentrationconcentrated to a brown oil
  5. customThe crude mixture was purified by silica gel column chromatography (hexane/ethyl acetate, 100/0 to 0/100)
  6. washby-product was eluted first (1.8 g)

출처 및 근거

ORD 기록
ord-48787509fcbd49089b41334e8d0e00ac
출처 데이터셋
uspto-grants-2003_03
특허 번호
US06537998B1

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