Sodium Methoxide → 2-Methoxy-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidine-4-carboxylic acid

HRID 216164

Reaction equation

HRID 216164 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[C:9]([NH:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[N:8]=[C:7](Cl)[N:6]=1)=[O:4].[CH3:23][O-:24].[Na+]>CO>[CH3:23][O:24][C:7]1[N:6]=[C:5]([C:3]([OH:2])=[O:4])[CH:10]=[C:9]([NH:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[N:8]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 576360902-Chloro-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidine-4-carboxylic acid methyl ester2×

Product 1

HCID 576360412-Methoxy-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidine-4-carboxylic acidYield 64%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A mixture of 2-chloro-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidine-4-carboxylic acid methyl ester [650 mg, 2.02 mmol, Intermediate (55)] 5M sodium methoxide in MeOH (20 mL, 10.1 mmol), in MeOH (10 mL) is heated to reflux and stirred for 5 hours. The heating is turned off and the mixture is stirred for 15 hours at room temperature and concentrated by rotary evaporator to remove the solvent. The solid is dissolved in water and the solution is acidified to pH 2 with the addition of 1N hydrochloric acid. Extracted three times with 75 mL EtOAc and concentrated the combined organic extracts to afford 2-methoxy-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidine-4-carboxylic acid [390 mg, 64%, Intermediate (56)] as a solid. LCMS: RT=1.99 minutes, MS: 304 (M+H).

Workup

  1. temperatureto reflux
  2. stirringthe mixture is stirred for 15 hours at room temperature
  3. concentrationconcentrated by rotary evaporator
  4. customto remove the solvent
  5. dissolutionThe solid is dissolved in water
  6. additionthe solution is acidified to pH 2 with the addition of 1N hydrochloric acid
  7. extractionExtracted three times with 75 mL EtOAc
  8. concentrationconcentrated the combined organic extracts

Sources & evidence

ORD record
ord-dedb29f5412b488fbb3557ece8939344
Source dataset
uspto-grants-2012_06
Patent number
US08193183B2

Linked notes

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