1,5-Dibromopentane → 5-mesityl-3,7-dimethyl-2-(piperidin-1-yl)-3H-pyrrolo[2,3-d]pyrimidin-4(7H)-one

HRID 598127노트

반응식

HRID 598127 반응식
[NH2:1][C:2]1[N:3]([CH3:22])[C:4](=[O:21])[C:5]2[C:10]([C:11]3[C:16]([CH3:17])=[CH:15][C:14]([CH3:18])=[CH:13][C:12]=3[CH3:19])=[CH:9][N:8]([CH3:20])[C:6]=2[N:7]=1.Br[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]Br.[H-].[Na+]>CN(C)C=O>[C:12]1([CH3:19])[CH:13]=[C:14]([CH3:18])[CH:15]=[C:16]([CH3:17])[C:11]=1[C:10]1[C:5]2[C:4](=[O:21])[N:3]([CH3:22])[C:2]([N:1]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)=[N:7][C:6]=2[N:8]([CH3:20])[CH:9]=1

참가 물질

5

반응물 3

HCID 81001,5-DibromopentaneHCID 24758Sodium hydrideHCID 672673282-Amino-5-mesityl-3,7-dimethyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

생성물 1

HCID 545829625-mesityl-3,7-dimethyl-2-(piperidin-1-yl)-3H-pyrrolo[2,3-d]pyrimidin-4(7H)-one수율 67.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 2-amino-5-mesityl-3,7-dimethyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one (0.063 g, 0.212 mmol) in N,N-dimethylformamide (1 mL) was added 1,5-dibromopentane (0.029 mL, 0.212 mmol) and sodium hydride (66% in oil, 0.015 g, 0.426 mmol) at 0° C., and the mixture was allowed to stir at room temperature for 1 hour. The reaction mixture was diluted with ice-cold water and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with hexane/ethyl acetate (10:1-3:1). The oil obtained was crystallized from diisopropyl ether-hexane to give 0.052 g (67%) of the title compound.

후처리

  1. additionThe reaction mixture was diluted with ice-cold water
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography
  7. washeluting with hexane/ethyl acetate (10:1-3:1)
  8. customThe oil obtained
  9. customwas crystallized from diisopropyl ether-hexane

출처 및 근거

ORD 기록
ord-52f95f159ddd4592b6026ca191602611
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07897607B2

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