Triethylamine → tert-butyl N-(2-chloropyridin-4-yl)carbamate

HRID 1092281Notes

Reaction equation

HRID 1092281 reaction equation
[C:1](OC([O-])=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CN(C1C=CC=CN=1)C.[NH2:21][C:22]1[CH:27]=[CH:26][N:25]=[C:24]([Cl:28])[CH:23]=1.C(N(CC)CC)C>ClCCl.O>[Cl:28][C:24]1[CH:23]=[C:22]([NH:21][C:1](=[O:2])[O:3][C:4]([CH3:7])([CH3:6])[CH3:5])[CH:27]=[CH:26][N:25]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 844322-Chloropyridin-4-amineHCID 22064466Tert-butyldicarbonate

Product 1

HCID 21858447tert-butyl N-(2-chloropyridin-4-yl)carbamateYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

1.69 g (7.78 mmol, 1 eq) of tert-butyl dicarbonate dissolved in 50 ml of dichloromethane, in the presence of 95 mg of dimethylaminopyridine, are added to a solution of 1 g (7.78 mmol, 1 eq) of 4-amino-2-chloropyridine in 30 mL of dichloromethane in the presence of 1.19 mL (1.19 mmol, 1.1 eq) of triethylamine. The reaction mixture is stirred overnight at room temperature. The reaction is stopped by adding 100 ml of water and is then extracted with dichloromethane. The organic phases are combined and dried over sodium sulfate. The solvents are evaporated off and the residue is then chromatographed on silica gel (70/30 to 50/50 heptane/ethyl acetate). The oil obtained is crystallized from pentane. 1.40 g of tert-butyl (2-chloropyrid-4-yl)carbamate are obtained. Yield=80%.

Workup

  1. extractionis then extracted with dichloromethane
  2. dry with materialdried over sodium sulfate
  3. customThe solvents are evaporated off
  4. customthe residue is then chromatographed on silica gel (70/30 to 50/50 heptane/ethyl acetate)
  5. customThe oil obtained
  6. customis crystallized from pentane

Sources & evidence

ORD record
ord-7ff335cb7e2243f9a969bfa6844ecf0c
Source dataset
uspto-grants-2012_03
Patent number
US08129416B2

Reaction notes

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