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Sodium borohydride → [1-(6-Tert-butyl-2-methoxypyridin-3-yl)ethyl]amine

HRID 1919836
Notes
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Reaction equation

HRID 1919836 reaction equation
[C:1]([C:5]1[N:10]=[CH:9][C:8]([CH:11]([NH2:13])[CH3:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(C1C=CC(C#N)=[C:20]([O:26]C)N=1)(C)(C)C.C[Mg+].[Br-].C1(C)C=CC=CC=1.C1COCC1.[BH4-].[Na+]>>[C:1]([C:5]1[N:10]=[C:9]([O:26][CH3:20])[C:8]([CH:11]([NH2:13])[CH3:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 5

HCID 4311764Sodium borohydrideHCID 22635083Tetrahydrofuran tolueneHCID 667452296-Tert-butyl-2-methoxynicotinonitrile2×HCID 67500288[1-(6-Tert-butylpyridin-3-yl)ethyl]amineHCID 178418689HCID 178418689, compound

Product 1

HCID 67499814
[1-(6-Tert-butyl-2-methoxypyridin-3-yl)ethyl]amine

Procedure

The title compound was synthesized according to the procedure described for the synthesis of [1-(6-tert-butylpyridin-3-yl)ethyl]amine starting from 6-tert-butyl-2-methoxynicotinonitrile (intermediate 23) (66 mg, 0.347 mmol), MeMgBr 1.4 M 75/25 toluene/THF (743 μL, 1.04 mmol) and NaBH4 (32.8 mg, 0.87 mmol Material isolated from the workup was used without further purification in the preparation.

Workup

  1. customisolated from the workup
  2. customwas used without further purification in the preparation

Sources & evidence

ORD record
ord-0e4bc44383f74a4dbcbaff24d437378a
Source dataset
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08168668B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes