2,6-Diaminopyridine → N-(6-Aminopyridin-2-yl)-2,2-dimethylpropanamide

HRID 987896Notes

Reaction equation

HRID 987896 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([NH2:8])[N:3]=1.[C:9](Cl)(=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11]>O1CCOCC1>[NH2:8][C:4]1[N:3]=[C:2]([NH:1][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])[CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 88612,6-DiaminopyridineHCID 62493Pivaloyl chloride

Product 1

HCID 15050440N-(6-Aminopyridin-2-yl)-2,2-dimethylpropanamideYield 74%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of 2,6-diaminopyridine (50.0 g, 0.46 mol) in dioxane (250 mL) was added slowly (1 h) pivaloylchloride (27.9 g, 0.23 mol), dissolved in dioxane (50 mL). The resulting mixture was stirred for 2 h and the white precipitate (2,6-diaminopyridine hydrochloride) filtered off. The organic phase was evaporated to dryness in vacuo, and the crude product recrystalized from n-hexane/ethyl acetate to give the desired product (32.83 g, 74%) as colorless crystals (mp 140-141° C.). 1H NMR (DMSO-d6): δ 8.93 (s, 1H), 7.34 (t, 7.9 Hz, 1H), 7.19 (d, 7.6 Hz, 1H), 6.18 (d, 7.6 Hz, 1H), 5.75 (br. s, 2H), 1.19 (s, 9H). 13C NMR (DMSO-d6): δ 176.5, 158.5, 150.4, 138.4, 103.6, 101.5, 39.4, 27.1. FAB+ MS (m/z): 193.88 M+H+, calc. for C10H15N3O+H+ 194.1293.

Workup

  1. filtrationthe white precipitate (2,6-diaminopyridine hydrochloride) filtered off
  2. customThe organic phase was evaporated to dryness in vacuo
  3. customthe crude product recrystalized from n-hexane/ethyl acetate

Sources & evidence

ORD record
ord-0b15964d70ac498983b25d445c65cd57
Source dataset
uspto-grants-2003_10
Patent number
US06632919B1

Reaction notes

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