Cesium carbonate → 1-isobutyl-6-(4-methoxybenzyl)-3,7-dimethyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

HRID 1423006노트

반응식

HRID 1423006 반응식
[CH2:1]([N:5]1[C:10]2=[C:11]([CH3:14])[NH:12][CH:13]=[C:9]2[C:8](=[O:15])[N:7]([CH3:16])[C:6]1=[O:17])[CH:2]([CH3:4])[CH3:3].Cl[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.O>[CH2:1]([N:5]1[C:10]2=[C:11]([CH3:14])[N:12]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=3)[CH:13]=[C:9]2[C:8](=[O:15])[N:7]([CH3:16])[C:6]1=[O:17])[CH:2]([CH3:4])[CH3:3]

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 699934-Methyloxybenzyl chlorideHCID 674148801-isobutyl-3,7-dimethyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

생성물 1

HCID 674155471-isobutyl-6-(4-methoxybenzyl)-3,7-dimethyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione수율 93.8%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

A suspension of 1-isobutyl-3,7-dimethyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione (78 mg, 0.33 mmol), 1-(chloromethyl)-4-methoxybenzene (88 μL, 0.63 mmol) and cesium carbonate (344 mg, 1.06 mmol) in anhydrous DMF is stirred at room temperature overnight. The mixture is diluted with 30 mL of water, and then extracted with CH2Cl2 three times. The combined organic phase is washed with brine, and then dried with anhydrous Na2SO4. After filtration, the filtrate is concentrated under vacuum. The residue is purified by basic alumina column chromatography to give 110 mg of product (yield: 93%). MS (ESI) m/z 356.2 [M+H]+.

후처리

  1. extractionextracted with CH2Cl2 three times
  2. washThe combined organic phase is washed with brine
  3. dry with materialdried with anhydrous Na2SO4
  4. filtrationAfter filtration
  5. concentrationthe filtrate is concentrated under vacuum
  6. customThe residue is purified by basic alumina column chromatography

출처 및 근거

ORD 기록
ord-8f8fe88c120345e5b429f9753ebddac6
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08927556B2

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