Imidazole → HCID 86723444, compound

HRID 2201200Notes

Reaction equation

HRID 2201200 reaction equation
[OH:1][CH:2]([CH2:23][OH:24])[CH2:3][N:4]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:11]2[C:6]([N:7]([CH3:22])[C:8](=[O:21])[N:9]([CH3:20])[C:10]2=[O:19])=[CH:5]1.N1C=CN=C1.[Si:30](Cl)([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31]>CN(C1C=CN=CC=1)C.CN(C=O)C.CCOC(C)=O>[Si:30]([O:24][CH2:23][CH:2]([OH:1])[CH2:3][N:4]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:11]2[C:6]([N:7]([CH3:22])[C:8](=[O:21])[N:9]([CH3:20])[C:10]2=[O:19])=[CH:5]1)([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31]

Participants

7

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chloride2×HCID 86723442HCID 86723442, compound

Product 1

HCID 86723444HCID 86723444, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

6-(2,3-Dihydroxypropyl)-1,3-dimethyl-5-phenyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione (step 1)(1.66 g, 5.04 mmol), imidazole (0.686 g, 10.08 mmol) and DMAP (0.062 g, 0.504 mmol) were dissolved in DMF (25 ml) and TBS-Cl (0.836 g, 5.54 mmol) was added. The resulting mixture was stirred at RT overnight. Further TBS-Cl (0.836 g, 5.54 mmol) added and stirring continued for 2 hours. The reaction mixture was diluted with EtOAc and washed with sat. NaHCO3(aq) and brine (3×). The organic phase was dried over sodium sulphate and evaporated under vacuum. The residue was redissolved in DCM and evaporated onto silica. The silica was deposited onto a 25 g silica cartridge and the system eluted with 20% EtOAc/hexane, 40% EtOAc/hexane and 60% EtOAc/hexane. The product fractions were combined and evaporated to give tacky yellow solid. This solid was triturated with Et2O/hexane to afford the title compound;

Workup

  1. stirringstirring
  2. waitcontinued for 2 hours
  3. washwashed with sat. NaHCO3(aq) and brine (3×)
  4. dry with materialThe organic phase was dried over sodium sulphate
  5. customevaporated under vacuum
  6. dissolutionThe residue was redissolved in DCM
  7. customevaporated onto silica
  8. washthe system eluted with 20% EtOAc/hexane, 40% EtOAc/hexane and 60% EtOAc/hexane
  9. customevaporated
  10. customto give tacky yellow solid
  11. customThis solid was triturated with Et2O/hexane

Sources & evidence

ORD record
ord-1a423302844446728978902cf33a03bc
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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