2-Aminopyridine → 2-(Pyridin-2-ylamino)-thiazole-5-carbonitrile

HRID 1355511Notes

Reaction equation

HRID 1355511 reaction equation
[H-].[Na+].[NH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1.Cl[C:11]1[S:12][C:13]([C:16]#[N:17])=[CH:14][N:15]=1>C1COCC1>[N:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[NH:3][C:11]1[S:12][C:13]([C:16]#[N:17])=[CH:14][N:15]=1

Participants

5

Reactant 3

HCID 104392-AminopyridineHCID 24758Sodium hydrideHCID 14852222-Chlorothiazole-5-carbonitrile

Product 1

HCID 53294022-(Pyridin-2-ylamino)-thiazole-5-carbonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A flame dried round-bottom flask under Ar was charged with NaH (60% dispersionm 0.037 g, 0.91 mmol). Anhydrous THF, 2 mL, was added followed by the addition of 2-aminopyridine (0.032 g, 0.033 mmol). 2-Chloro-thiazole-5-carbonitrile (9-2, 0.044 g, 0.30 mmol) was added and the reaction was heated to reflux. After 2 h the reaction was cooled and quenched by the addition of water. The THF was removed in vacuo and the precipitate which formed was filtered and washed with water. The solid was recrystallized from DMSO to provide a pure sample of the desired product. 1H NMR (DMSO-d6) d 12.23 (s, 1H), 8.40 (m, 1 h), 8.27 (s, 1H), 7.82 (m, 1H), 7.15 (d, 1H, J=8.3 Hz), 7.08 (m, 1H). MS [M+H]+=203.0.

Workup

  1. temperaturethe reaction was heated to reflux
  2. temperatureAfter 2 h the reaction was cooled
  3. customquenched by the addition of water
  4. customThe THF was removed in vacuo
  5. customthe precipitate which formed
  6. filtrationwas filtered
  7. washwashed with water
  8. customThe solid was recrystallized from DMSO

Sources & evidence

ORD record
ord-fc65d7aea9c64340a73b4658063db341
Source dataset
uspto-grants-2003_07
Patent number
US06586424B2

Reaction notes

Loading…