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

HRID 361371Notes

Reaction equation

HRID 361371 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 1M 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 1M 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-2803948956cd482697245cf1aff3c86c
Source dataset
uspto-grants-1999_02
Patent number
US05866573

Reaction notes

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