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

HRID 1423006Notes

Reaction equation

HRID 1423006 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

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]+.

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 basic alumina column chromatography

Sources & evidence

ORD record
ord-8f8fe88c120345e5b429f9753ebddac6
Source dataset
uspto-grants-2015_01
Patent number
US08927556B2

Reaction notes

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