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

HRID 859104Notes

Reaction equation

HRID 859104 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[CH:24]=[CH:23][N:22]=[C:21]([Cl:25])[CH:20]=3)[CH:16]=[CH:15][N:14]=2)[CH:9]=[CH:10][CH:11]=1)=[O:5])C.[OH-].[Li+]>C(O)C.O>[C:4]([C:6]1[CH:7]=[C:8]([NH:12][C:13]2[N:18]=[C:17]([C:19]3[CH:24]=[CH:23][N:22]=[C:21]([Cl:25])[CH:20]=3)[CH:16]=[CH:15][N:14]=2)[CH:9]=[CH:10][CH:11]=1)([OH:5])=[O:3]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 19689549N-[3-ethoxycarbonyl-phenyl]-4-(2-chloro4-pyridyl)-2-pyrimidineamine

Product 1

HCID 19689614N-[3-carboxy-phenyl]-4-(2-chloro-4-pyridyl)-2-pyrimidineamineYield 95.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of N-[3-ethoxycarbonyl-phenyl]-4-(2-chloro-4-pyridyl)-2-pyrimidineamine (860 mg, 2.43 mmol), lithium hydroxide (233 mg, 9.70 mmol) in ethanol (20 mL) and water (5 mL) is heated to reflux for 1 hour before cooling to room temperature. The mixture is concentrated, 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-4-pyridyl)-2-pyrimidineamine (760 mg); ESI-MS (m/z): 327.0 (M++H).

Workup

  1. temperatureis heated
  2. temperatureto reflux for 1 hour
  3. concentrationThe mixture is concentrated
  4. dissolutiondissolved in water
  5. filtrationThe solid is collected by filtration
  6. washwashed with water, methanol
  7. customdried

Sources & evidence

ORD record
ord-c834c0ccb3d4402abf46481861787d24
Source dataset
uspto-grants-2006_12
Patent number
US07151096B2

Reaction notes

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