Citric Acid → 4-(3-Chloro-4-methoxybenzylamino)-5-carboxy-6-methoxy-2-methylthiopyrimidine

HRID 917648Notes

Reaction equation

HRID 917648 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][C:23]=1[O:24][CH3:25])[CH2:5][NH:6][C:7]1[C:12]([C:13]([O:15]C)=[O:14])=[C:11]([O:17][CH3:18])[N:10]=[C:9]([S:19][CH3:20])[N:8]=1.[OH-].[Na+].O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CS(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][C:23]=1[O:24][CH3:25])[CH2:5][NH:6][C:7]1[C:12]([C:13]([OH:15])=[O:14])=[C:11]([O:17][CH3:18])[N:10]=[C:9]([S:19][CH3:20])[N:8]=1

Participants

6

Reactant 4

HCID 311Citric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 178483184-(3-Chloro-4-methoxybenzylamino)-5-methoxycarbonyl-6-methoxy-2-methylthiopyrimidine

Product 1

HCID 178483244-(3-Chloro-4-methoxybenzylamino)-5-carboxy-6-methoxy-2-methylthiopyrimidine

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 4-(3-chloro-4-methoxybenzylamino)-5-methoxycarbonyl-6-methoxy-2-methylthiopyrimidine (prepared in the above (1)) 271 mg, a 2.0M aqueous sodium hydroxide solution 3.53 ml, water 2 ml and dimethyl sulfoxide 6 ml is stirred at 65° C. for 14 hours. After cooling the reaction mixture is neutralized with a 10% aqueous citric acid solution and extracted with ethyl acetate. The ethyl acetate layer is washed, dried and concentrated in vacuo and the resulting powder is triturated with isopropyl ether to give 4-(3-chloro-4-methoxybenzylamino)-5-carboxy-6-methoxy-2-methylthiopyrimidine as a colorless crystalline powder, 210 mg. mp 167-170° C.

Workup

  1. temperatureAfter cooling the reaction mixture
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer is washed
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customthe resulting powder is triturated with isopropyl ether

Sources & evidence

ORD record
ord-afee58f1f9f9457c8f5b74d5abe3cb5e
Source dataset
uspto-grants-2007_09
Patent number
US07273868B2

Reaction notes

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