Dimethylamine → (4-tert-Butyl-6-chloro-pyridin-2-ylmethyl)-dimethylamine

HRID 1446721Notes

Reaction equation

HRID 1446721 reaction equation
[CH3:1][NH:2][CH3:3].C(N(CC)C(C)C)(C)C.Br[CH2:14][C:15]1[CH:20]=[C:19]([C:21]([CH3:24])([CH3:23])[CH3:22])[CH:18]=[C:17]([Cl:25])[N:16]=1.C(=O)(O)[O-].[Na+]>O1CCCC1>[C:21]([C:19]1[CH:18]=[C:17]([Cl:25])[N:16]=[C:15]([CH2:14][N:2]([CH3:3])[CH3:1])[CH:20]=1)([CH3:24])([CH3:23])[CH3:22]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 866343052-Bromomethyl-4-tert-butyl-6-chloro-pyridine

Product 1

HCID 86634306(4-tert-Butyl-6-chloro-pyridin-2-ylmethyl)-dimethylamineYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Stir a solution of 2N dimethylamine (9.00 mL, 18.08 mmol) in tetrahydrofuran, N,N-diisopropylethylamine (2.80 g, 3.80 mL, 21.69 mmol) while adding a solution of 2-bromomethyl-4-tert-butyl-6-chloro-pyridine (1.90 g, 7.23 mmol) in tetrahydrofuran (20 mL). Stir for 2.5 hours at ambient temperature, dilute the reaction with aqueous sodium bicarbonate (80 mL) and extract the aqueous layer with ethyl acetate (3×75 mL). Pool, desiccate, filter and concentrate the organics to yield the title compound (99%) (1.64 g, 7.23 mmol). MS(ES), m/z 227 (M+1).

Workup

  1. additiondilute
  2. extractionextract the aqueous layer with ethyl acetate (3×75 mL)
  3. filtrationPool, desiccate, filter
  4. concentrationconcentrate the organics

Sources & evidence

ORD record
ord-5cecbaf63360435eb679e54c4cfb4e3c
Source dataset
uspto-grants-2010_02
Patent number
US07666879B2

Reaction notes

Loading…