Bromotrimethylsilane → 2-Amino-5-mesityl-7-methyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

HRID 598118Notes

Reaction equation

HRID 598118 reaction equation
[C:1]1([CH3:12])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[CH2:9][CH:10]=O.Br[Si](C)(C)C.[NH2:18][C:19]1[N:24]=[C:23]([OH:25])[CH:22]=[C:21]([NH:26][CH3:27])[N:20]=1>O.C(=O)([O-])[O-].[K+].[K+].CS(C)=O.C(#N)C>[NH2:18][C:19]1[NH:24][C:23](=[O:25])[C:22]2[C:9]([C:2]3[C:3]([CH3:8])=[CH:4][C:5]([CH3:7])=[CH:6][C:1]=3[CH3:12])=[CH:10][N:26]([CH3:27])[C:21]=2[N:20]=1

Participants

8

Reactant 3

HCID 76113BromotrimethylsilaneHCID 3003822-(2,4,6-Trimethylphenyl)acetaldehydeHCID 178482274HCID 178482274, compound

Product 1

HCID 1364007122-Amino-5-mesityl-7-methyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-oneYield 68%

Reagents, catalysts & solvents 4

HCID 11430Potassium CarbonateCatalystHCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent2×

Procedure

A solution of dimethylsulfoxide (468 mg, 6.00 mmol) and acetonitrile (8 ml) was added to a mixture of mesitylacetoaldehyde (904 mg, 5.57 mmol), bromotrimethylsilane (919 mg, 6.00 mmol) and acetonitrile (8 ml) at 0° C. After stirring at room temperature for 0.5 hour, the mixture was diluted with water (70 ml) and extracted with ethyl acetate (100 ml×2). The extracts were combined, washed with brine, dried over sodium sulfate and concentrated in vacuo. A mixture of the residue, 2-amino-6-(methylamino)pyrimidin-4-ol (1.69 g, 6.00 mmol), potassium carbonate (50 mg) and dimethylsulfoxide (3 ml) was heated at 100° C. for 1 hour. After cooling, the mixture was diluted with water (100 ml) and extracted with ethyl acetate (100 ml×2). The extracts were combined, washed with saturated aqueous sodium hydrogen carbonate and brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel chromatography eluting with hexane/ethyl acetate (1:1) to give 1.07 g (68%) of the title compound.

Workup

  1. extractionextracted with ethyl acetate (100 ml×2)
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. temperaturewas heated at 100° C. for 1 hour
  6. temperatureAfter cooling
  7. extractionextracted with ethyl acetate (100 ml×2)
  8. washwashed with saturated aqueous sodium hydrogen carbonate and brine
  9. dry with materialdried over sodium sulfate
  10. concentrationconcentrated in vacuo
  11. customThe residue was purified by silica gel chromatography
  12. washeluting with hexane/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-57ac30eac20147f4b6bfeed75f1714b3
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

Loading…