Methanol → HCID 71279125, compound

HRID 1621135Notes

Reaction equation

HRID 1621135 reaction equation
[BH4-].[Li+].C[Si](C)(C)Cl.[CH3:8][C:9]1[C:10]([CH2:20][C:21]#[N:22])=[N:11][N:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:13]=1.CO>C1COCC1>[CH3:8][C:9]1[C:10]([CH2:20][CH2:21][NH2:22])=[N:11][N:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:13]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 6397ChlorotrimethylsilaneHCID 4148881Lithium borohydrideHCID 86677487HCID 86677487, compound

Product 1

HCID 71279125HCID 71279125, compoundYield 65.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To lithium borohydride (2M solution in THF, 629 μL, 1.26 mmol) was added dropwise trimethylchlorosilane (273 mg, 321 μL, 2.51 mmol) over a period of 5 min at 0-5° C. At that temperature a solution of 2-(4-methyl-1-phenyl-1H-pyrazol-3-yl)acetonitrile (62 mg, 314 μmol) in THF (0.5 mL) was added dropwise. The mixture was stirred at 70° C. for 1.5 h. After cooling down to 0-5° C., MeOH (0.5 mL) was added dropwise. After 10 min the ice bath was removed and the mixture was allowed to warm up to RT. The reaction mixture was poured into NaOH (1 M, 10 mL) and extracted with dichloromethane (3×25 mL). The combined organic layer was dried over MgSO4 and concentrated in vacuo to give the product as light yellow semisolid (46 mg, 206 μmol, 65.4%) which was used without further purification for the next step.

Workup

  1. temperatureAfter cooling down to 0-5° C.
  2. customAfter 10 min the ice bath was removed
  3. temperatureto warm up to RT
  4. additionThe reaction mixture was poured into NaOH (1 M, 10 mL)
  5. extractionextracted with dichloromethane (3×25 mL)
  6. dry with materialThe combined organic layer was dried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7b97726beec04c359546589eea58f7cd
Source dataset
uspto-grants-2014_07
Patent number
US08772510B2

Reaction notes

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