Cesium carbonate → 6-(4-(1H-1,2,4-triazol-1-yl)benzyl)-5-chloro-1-isobutyl-3-methyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

HRID 2205657Notes

Reaction equation

HRID 2205657 reaction equation
[Cl:1][C:2]1[NH:3][CH:4]=[C:5]2[C:10]=1[C:9](=[O:11])[N:8]([CH3:12])[C:7](=[O:13])[N:6]2[CH2:14][CH:15]([CH3:17])[CH3:16].Br[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]2[CH:30]=[N:29][CH:28]=[N:27]2)=[CH:22][CH:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.C(=O)(O)[O-].[Na+]>[N:26]1([C:23]2[CH:24]=[CH:25][C:20]([CH2:19][N:3]3[C:2]([Cl:1])=[C:10]4[C:5]([N:6]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:7](=[O:13])[N:8]([CH3:12])[C:9]4=[O:11])=[CH:4]3)=[CH:21][CH:22]=2)[CH:30]=[N:29][CH:28]=[N:27]1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 27764891-(4-(bromomethyl)phenyl)-1H-1,2,4-triazoleHCID 67415912HCID 67415912, compound

Product 1

HCID 701128166-(4-(1H-1,2,4-triazol-1-yl)benzyl)-5-chloro-1-isobutyl-3-methyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dioneYield 96.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A suspension of 5-chloro-1-isobutyl-3-methyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione (103 mg, 0.4 mmol), 1-(4-(bromomethyl)phenyl)-1H-1,2,4-triazole (93 mg, 0.48 mmol) and cesium carbonate (195 mg, 0.6 mmol) in anhydrous DMF (3 mL) is stirred at room temperature for 3 hours. The mixture is diluted with 20 mL of saturated sodium bicarbonate, and then extracted with CH2Cl2 three times. The combined organic phase is washed with brine, and then dried with anhydrous Na2SO4. After filtration through celite, the filtrate is concentrated to dryness under vacuum to give 160 mg of crude product as light brown solids, which is used in the next step without further purification. MS (ESI) m/z 413.2 [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 through celite
  5. concentrationthe filtrate is concentrated to dryness under vacuum

Sources & evidence

ORD record
ord-562e790218754594af60508044b0b106
Source dataset
uspto-grants-2016_06
Patent number
US09371327B2

Reaction notes

Loading…