Triethylamine → tert-Butyl 5-cyano-6-methylpyridin-2-ylcarbamate

HRID 850391Notes

Reaction equation

HRID 850391 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[N:9])=[C:4]([CH3:10])[N:3]=1.[O:11](C(OC(C)(C)C)=O)[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=O.C(N(CC)CC)C>CN(C1C=CN=CC=1)C.C(Cl)Cl.C(OCC)(=O)C>[C:15]([O:14][C:12]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[N:9])=[C:4]([CH3:10])[N:3]=1)=[O:11])([CH3:18])([CH3:17])[CH3:16]

Participants

7

Reactant 3

HCID 8471Triethylamine2×HCID 90495Di-tert-butyl dicarbonateHCID 27946626-Amino-2-methylpyridine-3-carbonitrile

Product 1

HCID 10704790tert-Butyl 5-cyano-6-methylpyridin-2-ylcarbamate

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-amino-5-cyano-6-methylpyridine (10.0 g, 75.1 mmol), (BOC)2O (16.39 g, 75.1 mmol), triethylamine (11.5 ml, 82.6 mmol) and DMAP (0.92 g, 7.5 mmol) in methylene chloride (200 ml) was stirred for 3 h. More triethylamine (4.22 ml) and (BOC2)O (1.64 g) were added and after 16 h the reaction was diluted with ethyl acetate and was washed with 1 M AcOH (3 times), dried (Na2SO4) and evaporated in vacuo to give dark brown solid. The crude product was purified by flash column chromatography (10% ethylacetate/hexanes) to give the title compound as a white solid:

Workup

  1. washwas washed with 1 M AcOH (3 times)
  2. dry with materialdried (Na2SO4)
  3. customevaporated in vacuo
  4. customto give dark brown solid
  5. customThe crude product was purified by flash column chromatography (10% ethylacetate/hexanes)

Sources & evidence

ORD record
ord-95be6324f0ce440b83b4247d25acbe91
Source dataset
uspto-grants-2000_01
Patent number
US06017934

Reaction notes

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