Triethylamine → 4-(3-Chloro-4-methoxybenzylamino)-5-carboxy-6-chloro-2-methylthiopyrimidine

HRID 917634

Reaction equation

HRID 917634 reaction equation
Cl[C:2]1[C:7]([C:8]([OH:10])=[O:9])=[C:6]([Cl:11])[N:5]=[C:4]([S:12][CH3:13])[N:3]=1.C(N(CC)CC)C.[Cl:21][C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][C:29]=1[O:30][CH3:31])[CH2:25][NH2:26]>CN(C)C=O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[Cl:21][C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][C:29]=1[O:30][CH3:31])[CH2:25][NH:26][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[C:6]([Cl:11])[N:5]=[C:4]([S:12][CH3:13])[N:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 7380383-Chloro-4-methoxybenzylamineHCID 220535774,6-Dichloro-2-(methylthio)pyrimidine-5-carboxylic acid

Product 1

HCID 178482684-(3-Chloro-4-methoxybenzylamino)-5-carboxy-6-chloro-2-methylthiopyrimidine

Reagents, catalysts & solvents 2

HCID 311Citric AcidSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a mixture of 4,6-dichloro-5-carboxy-2-methylthiopyrimidine (prepared in the above (1)) 500 mg and triethylamine 0.58 ml in dimethylformamide 3 ml is added 3-chloro-4-methoxybenzylamine 359 mg in dimethylformamide 3 ml at room temperature over a period of 15 minutes, and the mixture is stirred for 4 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-6-chloro-2-methylthiopyrimidine as a slightly brown powder.

Workup

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

Sources & evidence

ORD record
ord-4b8e76f03b9b457d80f969d895a0c3c6
Source dataset
uspto-grants-2007_09
Patent number
US07273868B2

Linked notes

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