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

HRID 917642Notes

Reaction equation

HRID 917642 reaction equation
[C:1]([C:4]1[C:5]([Cl:12])=[N:6][C:7]([Cl:11])=[N:8][C:9]=1Cl)([OH:3])=[O:2].[Cl:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][C:21]=1[O:22][CH3:23])[CH2:17][NH2:18].C(N(CC)CC)C>CN(C)C=O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[Cl:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][C:21]=1[O:22][CH3:23])[CH2:17][NH:18][C:9]1[C:4]([C:1]([OH:3])=[O:2])=[C:5]([Cl:12])[N:6]=[C:7]([Cl:11])[N:8]=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-dichloropyrimidine

Reagents, catalysts & solvents 2

HCID 311Citric AcidSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 5-carboxy-2,4,6-trichloropyrimidine 10.0 g in dimethylformamide 45 ml is added a suspension of 3-chloro-4-methoxybenzylamine 4.82 g and triethylamine 6.98 ml in dimethylformamide 40 ml over a period of 20 minutes on ice bath, and the mixture is stirred for 1 hour. The reaction mixture is diluted with a 10% aqueous citric acid solution and extracted with ethyl acetate. The organic layer is washed, dried and concentrated in vacuo to give 4-(3-chloro-4-methoxybenzylamino)-5-carboxy-2,6-dichloropyrimidine as a pale brown solid, 17.59 g. mp 150-151° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer is washed
  3. customdried
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c5f03332ff2d42d9a3927a30bf95c10d
Source dataset
uspto-grants-2007_09
Patent number
US07273868B2

Reaction notes

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