Sodium hydride → HCID 123961821, compound

HRID 1050352Notes

Reaction equation

HRID 1050352 reaction equation
[CH3:1][CH:2]([CH3:15])[C:3]([NH:5][C:6]1[N:14]=[CH:13][N:12]=[C:11]2[C:7]=1[NH:8][CH:9]=[N:10]2)=[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:8]1[C:7]2[C:11](=[N:12][CH:13]=[N:14][C:6]=2[NH:5][C:3](=[O:4])[CH:2]([CH3:15])[CH3:1])[N:10]=[CH:9]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 2817256HCID 2817256, compound

Product 1

HCID 123961821HCID 123961821, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 2-methyl-N-(7H-purin-6-yl)propanamide (1.5 g, 24.36 mmol) in dimethylformamide (20 mL), sodium hydride (0.88 g, 36.55 mmol) was added portion wise in 10 minutes at 0° C. The above suspension was stirred for 10 minutes at 0° C. followed by addition of 2-(trimethylsilyl)ethoxymethyl chloride (4.87 g, 29.24 mmol) slowly at 0° C. under nitrogen atmosphere. The reaction was stirred at room temperature for 16 h. After completion of the reaction, the mixture was quenched with saturated aqueous solution of ammonium chloride and product 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 2% methanol in dichloromethane. Concentration of the desired fractions afford 2-methyl-N-[7-(2-trimethylsilylethoxymethyl)purin-6-yl]propanamide (2) as white solid. Yield: 2 g, 24%.

Workup

  1. stirringThe reaction was stirred at room temperature for 16 h
  2. customAfter completion of the reaction
  3. customthe mixture was quenched with saturated aqueous solution of ammonium chloride and product
  4. extractionwas extracted with dichloromethane (2×50 mL)
  5. customThe organics were then separated
  6. dry with materialdried (magnesium sulfate)
  7. concentrationconcentrated to dryness under vacuum
  8. customthe crude was purified by flash chromatography
  9. washeluting with 2% methanol in dichloromethane

Sources & evidence

ORD record
ord-efcaf26916a341a78a2b1566df8c2b9d
Source dataset
uspto-grants-2016_07
Patent number
US09382248B2

Reaction notes

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