Imidazole → 6-(3-((tert-Butyldimethylsilyl)oxy)-2-hydroxypropyl)-5-(3-fluorophenyl)-1,3-dimethyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

HRID 2201207Notes

Reaction equation

HRID 2201207 reaction equation
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[OH:9][CH:10]([CH2:32][OH:33])[CH2:11][N:12]1[C:20]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=2)=[C:19]2[C:14]([N:15]([CH3:31])[C:16](=[O:30])[N:17]([CH3:29])[C:18]2=[O:28])=[CH:13]1.N1C=CN=C1>CN(C1C=CN=CC=1)C.CN(C=O)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[Si:1]([O:33][CH2:32][CH:10]([OH:9])[CH2:11][N:12]1[C:20]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=2)=[C:19]2[C:14]([N:15]([CH3:31])[C:16](=[O:30])[N:17]([CH3:29])[C:18]2=[O:28])=[CH:13]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

7

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 867234476-(2,3-Dihydroxypropyl)-5-(3-fluorophenyl)-1,3-dimethyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

Product 1

HCID 867234486-(3-((tert-Butyldimethylsilyl)oxy)-2-hydroxypropyl)-5-(3-fluorophenyl)-1,3-dimethyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 311Citric AcidSolventHCID 6228DimethylformamideSolvent

Procedure

Tert-butyldimethylsilyl chloride (0.695 g, 4.61 mmol) was added to a solution of 6-(2,3-dihydroxypropyl)-5-(3-fluorophenyl)-1,3-dimethyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione (1.82 g, 4.19 mmol), imidazole (0.571 g, 8.38 mmol) and DMAP (0.512 g, 4.19 mmol) in DMF (13.97 mL). The mixture was stirred at room temperature for 3 hours, then diluted with 10% aqueous citric acid solution (15 mL) and extracted with DCM (3×30 mL). The combined organic extracts were dried over magnesium sulfate and evaporated under vacuum. Purification by chromatography on silica, eluting with 0-50% EtOAc/hexane, afforded the title compound.

Workup

  1. extractionextracted with DCM (3×30 mL)
  2. dry with materialThe combined organic extracts were dried over magnesium sulfate
  3. customevaporated under vacuum
  4. customPurification by chromatography on silica
  5. washeluting with 0-50% EtOAc/hexane

Sources & evidence

ORD record
ord-75dcc3ed4fde42588b65aa9a181b12d4
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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