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

HRID 2386667Notes

Reaction equation

HRID 2386667 reaction equation
[OH-].[Na+].C([O:5][C:6]([C:8]1[C:9]([NH:16][CH:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)=[N:10][C:11]([S:14][CH3:15])=[N:12][CH:13]=1)=[O:7])C.Cl>CCO>[CH:17]1([NH:16][C:9]2[C:8]([C:6]([OH:7])=[O:5])=[CH:13][N:12]=[C:11]([S:14][CH3:15])[N:10]=2)[CH2:18][CH2:19][CH2:20][CH2:21]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 9151473Ethyl 4-(cyclopentylamino)-2-(methylsulfanyl)pyrimidine-5-carboxylate

Product 1

HCID 223298834-(Cyclopentylamino)-2-(methylsulfanyl)pyrimidine-5-carboxylic acidYield 97.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

NaOH (1 M aq, 31 mL) was added to a suspension of 4-cyclopentylamino-2-methylsulfanyl-pyrimidine-5-carboxylic acid ethyl ester (11.7 g, 41.6 mmol) in EtOH (14 mL) and the resulting mixture was heated at reflux for 1.5 h. The reaction mixture was cooled to RT and HCl (1 M aq) was added until pH 4 was reached. The white solid, which crashed out of solution, was collected by filtration, washed with water and heptane and then dried under reduced pressure to afford 10.241 g (97% yield) of 4-cyclopentylamino-2-methylsulfanyl-pyrimidine-5-carboxylic acid.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 1.5 h
  3. filtrationwas collected by filtration
  4. washwashed with water and heptane
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-5b0ce1d5da474ef597cc81994819fb4a
Source dataset
uspto-grants-2012_09
Patent number
US08268840B2

Reaction notes

Loading…