Chlorotrimethylsilane → HCID 67288108, compound

HRID 1626532Notes

Reaction equation

HRID 1626532 reaction equation
[BH4-].[Li+].Cl[Si](C)(C)C.[CH:8]1([C:11]2[N:16]=[C:15]([N:17]([CH3:19])[CH3:18])[C:14](/[CH:20]=[CH:21]/[N+:22]([O-])=O)=[CH:13][CH:12]=2)[CH2:10][CH2:9]1>C1COCC1>[NH2:22][CH2:21][CH2:20][C:14]1[C:15]([N:17]([CH3:18])[CH3:19])=[N:16][C:11]([CH:8]2[CH2:9][CH2:10]2)=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 4148881Lithium borohydrideHCID 67287927HCID 67287927, compound

Product 1

HCID 67288108HCID 67288108, compoundYield 98.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of lithium borohydride (1055 μL, 2.11 mmol) (in 2 mL of THF) was added chlorotrimethylsilane (535 μL, 4.22 mmol) dropwise. After stirring for 15 minutes, Argon was bubbled through the reaction mixture for 2 minutes to eliminate any trimethylsilane in the reaction mixture. (E)-6-Cyclopropyl-N,N-dimethyl-3-(2-nitrovinyl)pyridin-2-amine (123 mg, 0.527 mmol) was added (in 1 mL of THF). The reaction was heated to reflux for 2 hours, cooled to 0° C. and carefully quenched with methanol (1 mL). The reaction mixture was concentrated, diluted with dichloromethane and 20% aqueous KOH. The layers were separated and the organic layer was dried over sodium sulfate, filtered and concentrated to yield 3-(2-aminoethyl)-6-cyclopropyl-N,N-dimethylpyridin-2-amine (107 mg, 0.521 mmol, 98.8% yield).

Workup

  1. customArgon was bubbled through the reaction mixture for 2 minutes
  2. temperatureThe reaction was heated
  3. temperatureto reflux for 2 hours
  4. customcarefully quenched with methanol (1 mL)
  5. concentrationThe reaction mixture was concentrated
  6. additiondiluted with dichloromethane and 20% aqueous KOH
  7. customThe layers were separated
  8. dry with materialthe organic layer was dried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-4b9787dd791d414fb69f8bae00e557ef
Source dataset
uspto-grants-2014_07
Patent number
US08785445B2

Reaction notes

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