Sodium hydride → HCID 70981916, compound

HRID 1506115Notes

Reaction equation

HRID 1506115 reaction equation
[H-].[Na+].Cl[CH2:4][O:5][CH2:6][CH2:7][Si:8]([CH3:11])([CH3:10])[CH3:9].[CH:12]1([C:18]([C:20]2[C:21]3[CH:28]=[CH:27][NH:26][C:22]=3[N:23]=[CH:24][N:25]=2)=[O:19])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.C[SiH](C)C>CN(C)C=O.C1(C(C2C3C=CNC=3N=CN=2)=O)CCCCC1.O>[CH:12]1([C:18]([C:20]2[C:21]3[CH:28]=[CH:27][N:26]([CH2:4][O:5][CH2:6][CH2:7][Si:8]([CH3:11])([CH3:10])[CH3:9])[C:22]=3[N:23]=[CH:24][N:25]=2)=[O:19])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1

Participants

8

Reactant 4

HCID 24758Sodium hydride2×HCID 70435TrimethylsilaneHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 71258377HCID 71258377, compound

Product 1

HCID 70981916HCID 70981916, compoundYield 985.1%

Reagents, catalysts & solvents 3

HCID 71258377HCID 71258377, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

Cyclohexyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)methanone (50.0 mg, 0.218 mmol) in N,N-dimethylformamide (1 mL) was mixed with sodium hydride (60 wt % dispersion in mineral oil, 9.6 mg, 0.24 mmol) and [2-(chloromethoxy)ethyl]trimethylsilane (42.5 μL, 0.240 mmol) under cooling with ice and stirred for 30 minutes while the temperature was gradually raised to room temperature. Separately, cyclohexyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)methanone (500 mg, 2.18 mmol) in N,N-dimethylformamide (5 mL) was mixed with sodium hydride (60 wt % dispersion in mineral oil, 96 mg, 2.4 mmol) and (chloromethoxy)ethyl]trimethylsilane (425 μL, 2.40 mmol) under cooling with ice and stirred for 30 minutes while the temperature was gradually raised to room temperature. After addition of water, the reaction solution and the previously obtained reaction solution were extracted with ethyl acetate, respectively, and the organic layers were washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residues were combined and purified by silica gel column chromatography (hexane/ethyl acetate=5/1 (v/v)) to give the title compound as a pale yellow oil (850 mg, yield 99%).

Workup

  1. temperatureunder cooling with ice
  2. temperatureunder cooling with ice
  3. stirringstirred for 30 minutes while the temperature
  4. temperaturewas gradually raised to room temperature
  5. customthe reaction solution and the previously obtained reaction solution
  6. extractionwere extracted with ethyl acetate
  7. washrespectively, and the organic layers were washed with saturated aqueous sodium chloride
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. custompurified by silica gel column chromatography (hexane/ethyl acetate=5/1 (v/v))

Sources & evidence

ORD record
ord-c76ea69e04594d67bc297af1361fa10c
Source dataset
uspto-grants-2015_12
Patent number
US09216999B2

Reaction notes

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