Cesium carbonate → 6-(4-(6-fluoropyridin-2-yl)benzyl)-1-isobutyl-3-methyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

HRID 1422996노트

반응식

HRID 1422996 반응식
[CH2:1]([N:5]1[C:10]2=[CH:11][NH:12][CH:13]=[C:9]2[C:8](=[O:14])[N:7]([CH3:15])[C:6]1=[O:16])[CH:2]([CH3:4])[CH3:3].Cl[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[N:26]=2)=[CH:21][CH:20]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.O>[F:31][C:27]1[N:26]=[C:25]([C:22]2[CH:21]=[CH:20][C:19]([CH2:18][N:12]3[CH:13]=[C:9]4[C:10]([N:5]([CH2:1][CH:2]([CH3:4])[CH3:3])[C:6](=[O:16])[N:7]([CH3:15])[C:8]4=[O:14])=[CH:11]3)=[CH:24][CH:23]=2)[CH:30]=[CH:29][CH:28]=1

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 673706912-[4-(Chloromethyl)phenyl]-6-fluoropyridineHCID 674156251-isobutyl-3-methyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

생성물 1

HCID 674416686-(4-(6-fluoropyridin-2-yl)benzyl)-1-isobutyl-3-methyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione수율 71%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

A suspension of 1-isobutyl-3-methyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione (540 mg, 2.46 mmol), 2-(4-(chloromethyl)phenyl)-6-fluoropyridine (0.60 g, 2.7 mmol) and cesium carbonate (1.6 g, 4.9 mmol) in anhydrous DMF is stirred at room temperature for 10 minutes. The mixture is diluted with 200 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 silica gel chromatography to give product as pale yellow solids (705 mg, yield: 71%). MS (ESI) m/z 407.2 [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 silica gel chromatography

출처 및 근거

ORD 기록
ord-624ba45b45b841df8a4651d2d48b52d0
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08927556B2

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