Sodium Hydroxide → [4,6-Bis(dimethylamino)-2-{4-[4-(trifluoromethyl)benzamido]benzyl}-5-pyrimidinyl]acetic acid

HRID 1159672Notes

Reaction equation

HRID 1159672 reaction equation
[CH3:1][N:2]([CH3:37])[C:3]1[C:8]([CH2:9][C:10]([O:12]C)=[O:11])=[C:7]([N:14]([CH3:16])[CH3:15])[N:6]=[C:5]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([NH:24][C:25](=[O:36])[C:26]3[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=3)=[CH:20][CH:19]=2)[N:4]=1.[OH-].[Na+]>O1CCCC1.CO>[CH3:37][N:2]([CH3:1])[C:3]1[C:8]([CH2:9][C:10]([OH:12])=[O:11])=[C:7]([N:14]([CH3:15])[CH3:16])[N:6]=[C:5]([CH2:17][C:18]2[CH:19]=[CH:20][C:21]([NH:24][C:25](=[O:36])[C:26]3[CH:27]=[CH:28][C:29]([C:32]([F:34])([F:35])[F:33])=[CH:30][CH:31]=3)=[CH:22][CH:23]=2)[N:4]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 59514495HCID 59514495, compound

Product 1

HCID 45270144[4,6-Bis(dimethylamino)-2-{4-[4-(trifluoromethyl)benzamido]benzyl}-5-pyrimidinyl]acetic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl [4,6-bis(dimethylamino)-2-(4-{[4-(trifluoromethyl)benzoyl]amino}-benzyl)pyrimidin-5-yl]acetate (4.34 g, 8.42 mmol) in 20% tetrahydrofuran in methanol (100 mL) was treated with 1N sodium hydroxide solution (25 mL). The resulting mixture was heated at refluxing temperature for 5 hours and then the volatiles were removed by rotary evaporation under vacuum. The remaining aqueous solution was washed with diethyl ether and then neutralized with 1N hydrochloric acid at 0° C. The separated precipitate was collected by suction and rinsed with cold water. Recrystallization from methanol then gave [4,6-bis(dimethylamino)-2-(4-{[4-(trifluoromethyl)benzoyl]amino}benzyl)pyrimidin-5-yl]acetic acid (3.86 g, 81%) as colorless needles.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat refluxing temperature for 5 hours
  3. customthe volatiles were removed by rotary evaporation under vacuum
  4. washThe remaining aqueous solution was washed with diethyl ether
  5. customneutralized with 1N hydrochloric acid at 0° C
  6. customThe separated precipitate was collected by suction
  7. washrinsed with cold water
  8. customRecrystallization from methanol

Sources & evidence

ORD record
ord-35547a7078ff41349fd20032ea112562
Source dataset
uspto-grants-2010_10
Patent number
US07812160B2

Reaction notes

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