Methylamine → 6-(2-(Methylamino)pyrimidin-4-yloxy)-1-naphthoic acid

HRID 1925289Notes

Reaction equation

HRID 1925289 reaction equation
F[C:2]1[N:7]=[C:6]([O:8][C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[C:15]([C:19]([OH:21])=[O:20])=[CH:14][CH:13]=[CH:12]3)[CH:5]=[CH:4][N:3]=1.[CH3:22][NH2:23]>C1COCC1>[CH3:22][NH:23][C:2]1[N:7]=[C:6]([O:8][C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[C:15]([C:19]([OH:21])=[O:20])=[CH:14][CH:13]=[CH:12]3)[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 675205426-(2-Fluoropyrimidin-4-yloxy)-1-naphthoic acid

Product 1

HCID 248238976-(2-(Methylamino)pyrimidin-4-yloxy)-1-naphthoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6-(2-Fluoropyrimidin-4-yloxy)-1-naphthoic acid (step a, 1 g, 3.53 mmol) was suspended in THF (10 mL) and warmed to partially dissolve. The mixture was cooled to RT and N-methylamine (2 M in THF, 8.9 mL, 17.7 mmol) was added. After 2 h, the solvent was concentrated in-vacuo. The residue was diluted with H2O and made pH 7 using 1 N HCl. The solid was filtered and rinsed with water and Et2O to yield the title compound as a pink solid.

Workup

  1. temperaturewarmed
  2. dissolutionto partially dissolve
  3. concentrationthe solvent was concentrated in-vacuo
  4. additionThe residue was diluted with H2O
  5. filtrationThe solid was filtered
  6. washrinsed with water and Et2O

Sources & evidence

ORD record
ord-8e73769fc9c1478a95432dccd86accb2
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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