Azidotrimethylsilane → HCID 178438340, compound

HRID 354181Notes

Reaction equation

HRID 354181 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:14]2[NH:15][C:16](=[O:27])[C:17]3[C:18](=[C:20]([CH2:24][CH2:25][CH3:26])[N:21]([CH3:23])[N:22]=3)[N:19]=2)[C:6]([O:9][CH2:10][CH:11]([CH3:13])[CH3:12])=[N:7][CH:8]=1)#[CH:2].C[Si]([N:32]=[N+:33]=[N-:34])(C)C>>[CH2:10]([O:9][C:6]1[C:5]([C:14]2[NH:15][C:16](=[O:27])[C:17]3[C:18](=[C:20]([CH2:24][CH2:25][CH3:26])[N:21]([CH3:23])[N:22]=3)[N:19]=2)=[CH:4][C:3]([C:1]2[NH:34][N:33]=[N:32][CH:2]=2)=[CH:8][N:7]=1)[CH:11]([CH3:13])[CH3:12]

Participants

3

Reactant 2

HCID 78378AzidotrimethylsilaneHCID 135730585HCID 135730585, compound

Product 1

HCID 178438340HCID 178438340, compoundYield 49.4%

Procedure

5-(5-Ethynyl-2-isobutoxy-3-pyridinyl)-2-methyl-3-propyl-2,6-dihydro-7H-pyrazolo[4,3-a]pyrimidin-7-one (Example 27) (200 mg, 0.54 mmol) and trimethylsilylazide (630 mg, 5.4 mmol) were stirred at 170° C. in a sealed pressure vessel for 14 h. The reaction mixture was cooled and partitioned between ethyl acetate and saturated sodium bicarbonate solution. The brown precipitate was filtered off and the 2 phases separated. The organic phase was washed with more sodium bicarbonate solution and brine, dried with (MgSO4) and concentrated. This residue was combined with the original precipitate and purified by flash column chromatography (gradient elution from dichloromethane to 5% methanol:dichloromethane) to give 109 mg of a white solid (49%).

Workup

  1. temperatureThe reaction mixture was cooled
  2. custompartitioned between ethyl acetate and saturated sodium bicarbonate solution
  3. filtrationThe brown precipitate was filtered off
  4. customthe 2 phases separated
  5. washThe organic phase was washed with more sodium bicarbonate solution and brine
  6. dry with materialdried with (MgSO4)
  7. concentrationconcentrated
  8. custompurified by flash column chromatography (gradient elution from dichloromethane to 5% methanol:dichloromethane)

Sources & evidence

ORD record
ord-1686af1b3e7e4569801f25dcbd230f9b
Source dataset
uspto-grants-2004_06
Patent number
US06756373B1

Reaction notes

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