Hydrochloric Acid → HCID 55273099, compound

HRID 2069386Notes

Reaction equation

HRID 2069386 reaction equation
C([O:3][C:4]([C:6]1[CH:11]=[C:10]([CH2:12][CH3:13])[N:9]=[C:8]([S:14][CH3:15])[N:7]=1)=[O:5])C.Cl>C(O)C.C1COCC1.[Li+].[OH-]>[CH2:12]([C:10]1[N:9]=[C:8]([S:14][CH3:15])[N:7]=[C:6]([C:4]([OH:5])=[O:3])[CH:11]=1)[CH3:13]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 66933611HCID 66933611, compound

Product 1

HCID 55273099HCID 55273099, compoundYield 98.6%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 3939Lithium HydroxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-ethyl-2-methylsulfanyl-pyrimidine-4-carboxylic acid ethyl ester (590 mg, 2.61 mmol) in ethanol (12 mL) and THF (12 mL), 2M aq. LiOH (4 mL) is added. The mixture is stirred for 12 h at rt before neutralizing with 1N aq. HCl. The aq. solution is extracted 3 times with ethylacetate and the combined org. layers are evaporated to dryness to give 510 mg of 6-ethyl-2-methylsulfanyl-pyrimidine-4-carboxylic acid as a white solid; LC-MS: tR=0.75 min, [M+H]+=199.02.

Workup

  1. extractionThe aq. solution is extracted 3 times with ethylacetate
  2. customlayers are evaporated to dryness

Sources & evidence

ORD record
ord-fe577e04b9f342338625eb6bd368563e
Source dataset
uspto-grants-2012_10
Patent number
US08299086B2

Reaction notes

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