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 1422996ノート

反応式

HRID 1422996 の反応式
[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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-624ba45b45b841df8a4651d2d48b52d0
出典データセット
uspto-grants-2015_01
特許番号
US08927556B2

反応ノート

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