Isopropyl iodide → 6-Bromo-8-isopropyl-4-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one

HRID 2389969노트

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HRID 2389969 반응식
[H-].[Na+].[Br:3][C:4]1[C:16](=[O:17])[NH:15][C:7]2[N:8]=[C:9]([S:13][CH3:14])[N:10]=[C:11]([CH3:12])[C:6]=2[CH:5]=1.I[CH:19]([CH3:21])[CH3:20]>CN(C=O)C>[Br:3][C:4]1[C:16](=[O:17])[N:15]([CH:19]([CH3:21])[CH3:20])[C:7]2[N:8]=[C:9]([S:13][CH3:14])[N:10]=[C:11]([CH3:12])[C:6]=2[CH:5]=1

참가 물질

5

반응물 3

HCID 6362Isopropyl iodideHCID 24758Sodium hydrideHCID 592589096-bromo-4-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one

생성물 1

HCID 592589536-Bromo-8-isopropyl-4-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one수율 59.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
46 °C

실험 절차

To a suspension of NaH (120 mg, 5.00 mmol) in DMF (15 mL) was added 6-bromo-4-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one (572 mg, 2 mmol). The mixture was heated to 46° C. The solution was cooled down slightly and 2-iodopropane (0.30 mL, 3.0 mmol) was added. The mixture was heated at 46° C. for 30 min and then cooled to room temperature and partitioned between water and ethyl acetate. The organic phase was dried (MgSO4) and concentrated. The crude product was purified by silica gel flash chromatography, using EtOAc/Hexane, to give the title compound (390 mg, 59%).

후처리

  1. temperatureThe solution was cooled down slightly
  2. temperatureThe mixture was heated at 46° C. for 30 min
  3. temperaturecooled to room temperature
  4. custompartitioned between water and ethyl acetate
  5. dry with materialThe organic phase was dried (MgSO4)
  6. concentrationconcentrated
  7. customThe crude product was purified by silica gel flash chromatography

출처 및 근거

ORD 기록
ord-0742ec46b387422ca53ca4115c308c1c
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08273755B2

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