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

HRID 1246724Notes

Reaction equation

HRID 1246724 reaction equation
Cl[C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[NH:8]1[CH2:13][CH:12]=[C:11]([C:14]([OH:16])=[O:15])[CH2:10][CH2:9]1>O>[N:3]1[CH:4]=[CH:5][CH:6]=[N:7][C:2]=1[N:8]1[CH2:9][CH:10]=[C:11]([C:14]([OH:16])=[O:15])[CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 3765Isoguvacine2×HCID 744042-Chloropyrimidine

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

2-Chloropyrimidine (0.570 g, 4.98 mmol) and 1,2,3,6-tetrahydro-4-pyridinecarboxylic acid (1.22 g) were combined in water (7 mL) and heated at 90° C. After 4 hours, the mixture was treated with additional 1,2,3,6-tetrahydro-4-pyridinecarboxylic acid (0.52 g) and stirred overnight. The mixture was diluted with water and extracted with CH2Cl2. The aqueous layer was acidified with concentrated HCl (pH˜3) and extracted with CHCl3. The organic layer was dried (Na2SO4), filtered, and the filtrate was concentrated under reduced pressure to provide the title.

Workup

  1. extractionextracted with CH2Cl2
  2. extractionextracted with CHCl3
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customto provide the title

Sources & evidence

ORD record
ord-d4dc0185bf73494b8f3512f45855857c
Source dataset
uspto-grants-2006_10
Patent number
US07129235B2

Reaction notes

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