Sodium hydride → HCID 131736067, compound

HRID 1050373Notes

Reaction equation

HRID 1050373 reaction equation
[CH3:1][CH:2]([CH3:15])[C:3]([NH:5][C:6]1[C:7]2[N:14]=[N:13][NH:12][C:8]=2[N:9]=[CH:10][N:11]=1)=[O:4].[H-].[Na+].[CH3:18][Si:19]([CH3:26])([CH3:25])[CH2:20][CH2:21][O:22][CH2:23]Cl>CN(C)C=O>[CH3:18][Si:19]([CH3:26])([CH3:25])[CH2:20][CH2:21][O:22][CH2:23][N:5]([C:6]1[C:7]2[N:14]=[N:13][N:12]([CH2:23][O:22][CH2:21][CH2:20][Si:19]([CH3:26])([CH3:25])[CH3:18])[C:8]=2[N:9]=[CH:10][N:11]=1)[C:3](=[O:4])[CH:2]([CH3:15])[CH3:1]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 178454500HCID 178454500, compound

Product 1

HCID 131736067HCID 131736067, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 2-methyl-N-(3H-triazolo[4,5-d]pyrimidin-7-yl)propanamide (3, 1.5 g, 7.27 mmol) in dimethylformamide (20 mL), sodium hydride (0.26 g, 10.91 mmol) was added portion wise in 10 min at 0° C. The above suspension was stirred for 10 min at 0° C. and 2-(trimethylsilyl)ethoxymethyl chloride (1.82 g, 10.91 mmol) was added at the same temperature under nitrogen. The reaction was stirred at room temperature for 6 h. After completion, the reaction mass was quenched with saturated aqueous solution of ammonium chloride and crude was extracted with dichloromethane (2×50 mL). The organics were then separated, dried (magnesium sulfate) and concentrated to dryness under vacuum and the crude was purified by flash chromatography eluting with 5% ethyl acetate in hexane. Concentration of the desired fractions provides 2-methyl-N-(2-trimethylsilylethoxy)-N-[3-(2-trimethylsilylethoxyl)triazolo[4,5-d]pyrimidin-7-yl]propanamide (4) as transparent viscous oil. Yield: 1.1 g, 44%; MS (ESI) m/z 467.42 [M+1]+.

Workup

  1. stirringThe reaction was stirred at room temperature for 6 h
  2. customAfter completion, the reaction mass was quenched with saturated aqueous solution of ammonium chloride and crude
  3. extractionwas extracted with dichloromethane (2×50 mL)
  4. customThe organics were then separated
  5. dry with materialdried (magnesium sulfate)
  6. concentrationconcentrated to dryness under vacuum
  7. customthe crude was purified by flash chromatography
  8. washeluting with 5% ethyl acetate in hexane

Sources & evidence

ORD record
ord-edf7801af2344e7fa1822aa2c604ceb9
Source dataset
uspto-grants-2016_07
Patent number
US09382248B2

Reaction notes

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