Sodium Hydroxide → N-[3-carboxy-phenyl]-4-(2-chloro-3-pyridyl)-2-pyrimidineamine

HRID 859107Notes

Reaction equation

HRID 859107 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[C:8]([NH:12][C:13]2[N:18]=[C:17]([C:19]3[C:20]([Cl:25])=[N:21][CH:22]=[CH:23][CH:24]=3)[CH:16]=[CH:15][N:14]=2)[CH:9]=[CH:10][CH:11]=1)=[O:5])C.[OH-].[Na+]>C(#N)C.O>[C:4]([C:6]1[CH:7]=[C:8]([NH:12][C:13]2[N:18]=[C:17]([C:19]3[C:20]([Cl:25])=[N:21][CH:22]=[CH:23][CH:24]=3)[CH:16]=[CH:15][N:14]=2)[CH:9]=[CH:10][CH:11]=1)([OH:5])=[O:3]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86595099N-[3-ethoxycarbonyl-phenyl]-4-(2-chloro-3-pyridyl)-2-pyrimidineamine

Product 1

HCID 85993175N-[3-carboxy-phenyl]-4-(2-chloro-3-pyridyl)-2-pyrimidineamineYield 56.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of N-[3-ethoxycarbonyl-phenyl]-4-(2-chloro-3-pyridyl)-2-pyrimidineamine (1.15 g, 3.24 mmol), sodium hydroxide (300 mg, 7.5 mmol) in acetonitrile (15 mL) and water (5 mL) is heated to reflux for 4 hours. The reaction mixture is then cooled to room temperature and concentrated. The residue is dissolved in water and acidified with 10% hydrochloric acid. The solid is collected by filtration and washed with water, methanol and dried to give N-[3-carboxy-phenyl]-4-(2-chloro-3-pyridyl)-2-pyrimidineamine (600 mg); ESI-MS (m/z): 327.0 (M++H).

Workup

  1. temperatureis heated
  2. temperatureto reflux for 4 hours
  3. concentrationconcentrated
  4. dissolutionThe residue is dissolved in water
  5. filtrationThe solid is collected by filtration
  6. washwashed with water, methanol
  7. customdried

Sources & evidence

ORD record
ord-ea17667f5e7f480e95cf1b3d6a3d9413
Source dataset
uspto-grants-2006_12
Patent number
US07151096B2

Reaction notes

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