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 1422996Notes

Reaction equation

HRID 1422996 reaction equation
[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

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

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]+.

Workup

  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

Sources & evidence

ORD record
ord-624ba45b45b841df8a4651d2d48b52d0
Source dataset
uspto-grants-2015_01
Patent number
US08927556B2

Reaction notes

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