Cesium carbonate → 5-(3-{[tert-butyl(dimethyl)silyl]oxy}propyl)-4-chloro-5H-pyrrolo[3,2-d]pyrimidine

HRID 1925999Notes

Reaction equation

HRID 1925999 reaction equation
[Cl:1][C:2]1[C:3]2[NH:10][CH:9]=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:18][CH2:19][CH2:20][O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23]>CN(C)C=O.O>[Si:22]([O:21][CH2:20][CH2:19][CH2:18][N:10]1[C:3]2[C:2]([Cl:1])=[N:7][CH:6]=[N:5][C:4]=2[CH:8]=[CH:9]1)([C:25]([CH3:26])([CH3:27])[CH3:28])([CH3:24])[CH3:23]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 607486(3-Bromopropoxy)(tert-butyl)dimethylsilaneHCID 53706954-chloro-5H-pyrrolo[3,2-d]pyrimidine

Product 1

HCID 866157565-(3-{[tert-butyl(dimethyl)silyl]oxy}propyl)-4-chloro-5H-pyrrolo[3,2-d]pyrimidineYield 74.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of 4-chloro-5H-pyrrolo[3,2-d]pyrimidine (400 mg) in N,N-dimethylformamide (2.6 mL) was added cesium carbonate (957 mg) under ice-cooling, and the mixture was stirred while warming to room temperature for 15 min. To the reaction mixture was added (3-bromopropoxy)(tert-butyl)dimethylsilane (979 mg), and the mixture was stirred at room temperature for 16 hrs. The reaction mixture was diluted with water (20 mL) and extracted with ethyl acetate (30 mL×3). The organic layer was washed with saturated brine (30 mL×3) and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was subjected to silica gel column chromatography (silica gel, eluent:hexane/ethyl acetate=85/15→10/90). The object fraction was concentrated under reduced pressure and dried to give the title compound (630 mg) as a white solid.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 16 hrs
  3. extractionextracted with ethyl acetate (30 mL×3)
  4. washThe organic layer was washed with saturated brine (30 mL×3)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. concentrationThe object fraction was concentrated under reduced pressure
  8. customdried

Sources & evidence

ORD record
ord-d07a3e43b9d8475e91c361ccf00e9171
Source dataset
uspto-grants-2012_05
Patent number
US08178543B2

Reaction notes

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