Triethylamine → 4-(3-Chloro-4-methoxybenzylamino)-5-carboxy-2,6-dichloropyrimidine

HRID 917628Notes

Reaction equation

HRID 917628 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH2:5][NH2:6].C(N(CC)CC)C.[C:19]([C:22]1[C:23]([Cl:30])=[N:24][C:25]([Cl:29])=[N:26][C:27]=1Cl)([OH:21])=[O:20]>CN(C)C=O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH2:5][NH:6][C:27]1[C:22]([C:19]([OH:21])=[O:20])=[C:23]([Cl:30])[N:24]=[C:25]([Cl:29])[N:26]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 7380383-Chloro-4-methoxybenzylamineHCID 200839572,4,6-Trichloropyrimidine-5-carboxylic acid

Product 1

HCID 178482874-(3-Chloro-4-methoxybenzylamino)-5-carboxy-2,6-dichloropyrimidineYield 91.6%

Reagents, catalysts & solvents 2

HCID 311Citric AcidSolventHCID 6228DimethylformamideSolvent2×

Procedure

A N,N-dimethylformamide solution 6 ml of 3-chloro-4-methoxybenzylamine 1.51 g and triethylamine 2.46 g is dropped over a period of 25 minutes under ice cooling a solution of 5-carboxy-2,4,6-trichloropyrimidine (prepared in Example 318(1)) 2.00 g in N,N-dimethylformamide 12 ml, and the mixture is further stirred for 90 minutes. The reaction mixture is diluted with a 10% aqueous citric acid solution and extracted with ethyl acetate. The combined extract is washed with water and an aqueous sodium chloride solution, dried over anhydrous sodium sulfate and concentrated in vacuo to give 4-(3-chloro-4-methoxybenzylamino)-2,6-dichloropyrimidine-5-carboxylic acid as a pale brown crystalline powder 2.92 g. mp 144-151° C.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe combined extract
  3. washis washed with water
  4. dry with materialan aqueous sodium chloride solution, dried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5fb491e0410846a882be6f0e025184bf
Source dataset
uspto-grants-2007_09
Patent number
US07273868B2

Reaction notes

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