Caffeine → ethyl 2-((1,3,7-trimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl)methyl)acrylate

HRID 522507

반응식

HRID 522507 반응식
[Li+].[Cl-].[CH3:3][N:4]1[C:12](=[O:13])[C:11]2[N:10]([CH3:14])[CH:9]=[N:8][C:7]=2[N:6]([CH3:15])[C:5]1=[O:16].Br[CH2:18][C:19](=[CH2:25])[C:20]([O:22][CH2:23][CH3:24])=[O:21].C([Cu])#N>C1COCC1>[CH3:3][N:4]1[C:12](=[O:13])[C:11]2[N:10]([CH3:14])[C:9]([CH2:25][C:19](=[CH2:18])[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[N:8][C:7]=2[N:6]([CH3:15])[C:5]1=[O:16]

참가 물질

6

반응물 4

HCID 2519CaffeineHCID 3106202-(Bromomethyl)acrylic acid ethyl esterHCID 433294Lithium ChlorideHCID 178418546HCID 178418546, 화합물

생성물 1

HCID 58526534ethyl 2-((1,3,7-trimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl)methyl)acrylate수율 69%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-50 °C

실험 절차

TMPZnCl.LiCl (2) (1.3 M in THF, 0.85 mL, 1.1 mmol) was added to a solution of 1,3,7-trimethyl-1H-purine-2,6(3H,7H)-dione (12) (194 mg, 1.0 mmol) in THF (2 mL) at 25° C. and the reaction mixture was then stirred at this temperature for max. 5 min. After cooling down to −50 ° C., ethyl 2-(bromomethyl)acrylate (230 mg, 1.2 mmol) and CuCN.2LiCl (1.0 M solution in THF, 5 drops) were added and the resulting mixture was allowed to warm up slowly overnight. The reaction mixture was quenched with a sat. aq. NH4Cl solution (20 mL), extracted with diethyl ether (3×50 mL) and dried over anhydrous Na2SO4. After filtration, the solvent was evaporated in vacuo. Purification by flash-chromatography (CH2Cl2/ether, 1:1) furnished compound 14b (211 mg, 69%) as a colourless solid.

후처리

  1. custom5 min
  2. temperatureto warm up slowly overnight
  3. customThe reaction mixture was quenched with a sat. aq. NH4Cl solution (20 mL)
  4. extractionextracted with diethyl ether (3×50 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationAfter filtration
  7. customthe solvent was evaporated in vacuo
  8. customPurification by flash-chromatography (CH2Cl2/ether, 1:1)

출처 및 근거

ORD 기록
ord-543c1b1ba79a4416a7ec9715cd78226f
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09334237B2

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