Hydrochloric Acid → 4-(2-Bromo-phenyl)-2-methylsulfanyl-pyrimidine-5-carboxylic acid

HRID 650633Notes

Reaction equation

HRID 650633 reaction equation
C([O:3][C:4]([C:6]1[C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[Br:20])=[N:8][C:9]([S:12][CH3:13])=[N:10][CH:11]=1)=[O:5])C.O.C(Cl)Cl.Cl>C(O)C>[Br:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[C:7]1[C:6]([C:4]([OH:5])=[O:3])=[CH:11][N:10]=[C:9]([S:12][CH3:13])[N:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 6344DichloromethaneHCID 54014435HCID 54014435, compound

Product 1

HCID 217124834-(2-Bromo-phenyl)-2-methylsulfanyl-pyrimidine-5-carboxylic acidYield 98.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5.10 g (14.4 mmol) 4-(2-bromo-phenyl)-2-methylsulfanyl-pyrimidine-5-carboxylic acid ethyl ester in 10 ml ethanol 10 ml 2N NaOH-solution were added. After stirring for 1 hr. 50 ml H2O and 50 ml CH2Cl2 were added to the yellow solution.The pH of the aqueous phase was adjusted to 1 with 25% HCl the phases separated and the aqueous phase extracted twice with 200 ml CH2Cl2. The combined organic layers were dried (MgSO4), filtrated and evaporated to give 4.60 g (98%) 4-(2-bromo-phenyl)-2-methylsulfanyl-pyrimidine-5-carboxylic acid as a off-white solid.

Workup

  1. customseparated
  2. extractionthe aqueous phase extracted twice with 200 ml CH2Cl2
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. filtrationfiltrated
  5. customevaporated

Sources & evidence

ORD record
ord-19d4e9d26af74c769fbedc681af7afbe
Source dataset
uspto-grants-2001_08
Patent number
US06274588B1

Reaction notes

Loading…