Lithium Hexamethyldisilazide → HCID 57929471, compound

HRID 2386678Notes

Reaction equation

HRID 2386678 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[C:11]([C:13]1[C:14]([N:21]([CH:25]2[CH2:28][CH2:27][CH2:26]2)[C:22](=[O:24])[CH3:23])=[N:15][C:16]([S:19][CH3:20])=[N:17][CH:18]=1)#[N:12]>C1COCC1>[NH2:12][C:11]1[C:13]2[CH:18]=[N:17][C:16]([S:19][CH3:20])=[N:15][C:14]=2[N:21]([CH:25]2[CH2:26][CH2:27][CH2:28]2)[C:22](=[O:24])[CH:23]=1

Participants

4

Reactant 2

HCID 2733832Lithium HexamethyldisilazideHCID 57929452HCID 57929452, compound

Product 1

HCID 57929471HCID 57929471, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of lithium bis(trimethylsilyl)amide (1.0 M in THF, 0.78 mL, 0.781 mmol) was added, at RT, to a solution of N-(5-cyano-2-methylsulfanyl-pyrimidin-4-yl)-N-cyclobutyl-acetamide (205 mg, 0.781 mmol) in THF (7.8 mL) and the resulting mixture was stirred for 1 h. The reaction mixture was then quenched with water (10 mL) and extracted with EtOAc (2×20 mL). The combined organic extracts were dried over MgSO4, filtered and evaporated under reduced pressure. The crude residue was purified by flash chromatography (MeOH/DCM, 1/99 to 5/95 in 10 min) to afford 98 mg (48% yield) as a white solid. MS=263 [M+H]+.

Workup

  1. customThe reaction mixture was then quenched with water (10 mL)
  2. extractionextracted with EtOAc (2×20 mL)
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe crude residue was purified by flash chromatography (MeOH/DCM, 1/99 to 5/95 in 10 min)
  7. customto afford 98 mg (48% yield) as a white solid

Sources & evidence

ORD record
ord-3f17074d911c431f98b157d330bb05e6
Source dataset
uspto-grants-2012_09
Patent number
US08268840B2

Reaction notes

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