Isoguvacine → 1-Pyrimidin-2-yl-1,2,3,6-tetrahydropyridine-4-carboxylic acid

HRID 1394099Notes

Reaction equation

HRID 1394099 reaction equation
Cl[C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[CH2:8]1[C:13]([C:14]([OH:16])=[O:15])=[CH:12][CH2:11][NH:10][CH2:9]1.[Na]>O>[N:3]1[CH:4]=[CH:5][CH:6]=[N:7][C:2]=1[N:10]1[CH2:9][CH:8]=[C:13]([C:14]([OH:16])=[O:15])[CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 3765Isoguvacine2×HCID 744042-ChloropyrimidineHCID 5360545Sodium2×

Product 1

HCID 219047301-Pyrimidin-2-yl-1,2,3,6-tetrahydropyridine-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
90 °C

Procedure

A mixture of 2-chloropyrimidine (0.570 g, 4.98 mmol), and isoguvacine, sodium salt (1.2 g, 8.2 mmol) in water (7 mL) was heated to 90° C. and stirred for 4 hour. Additional isoguvacine, sodium salt (0.52 g, 3.3 mmol) was then added and stirred overnight. The mixture was diluted with water and extracted with CH2Cl2. The aqueous layer was acidified with conc HCl (pH˜3) and extracted with CHCl3. The organic layer was dried (Na2SO4), filtered and concentrated under reduced pressure to provide 1-Pyrimidin-2-yl-1,2,3,6-tetrahydro-pyridine-4-carboxylic acid a white solid (0.564 g, 2.75 mmol, 55%): 1H NMR (300 MHz, CD3OD) δ 8.43 (d, J=4.8 Hz, 2H), 7.02 (sept, J=1.7 Hz, 1H), 6.74 (t, J=4.8 Hz, 1H), 4.39 (q, J=3.0 Hz, 2H), 3.97 (t, J=5.8 Hz, 2H), 2.49 (m, 2H).

Workup

  1. stirringstirred overnight
  2. extractionextracted with CH2Cl2
  3. extractionextracted with CHCl3
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-dc4bfa60c10245d0a4763498749ddb7a
Source dataset
uspto-grants-2008_03
Patent number
US07348343B2

Reaction notes

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