Hydrochloric Acid → 6-Hydroxy-2-(methylthio)-4-pyrimidinecarboxylic acid

HRID 68300

Reaction equation

HRID 68300 reaction equation
[C:1]([O:11]CC)(=O)[CH2:2][C:3]([C:5]([O:7]CC)=[O:6])=O.[OH-].[Na+].S(O)(O)(=O)=O.[CH3:21][S:22][C:23](=[NH:25])[NH2:24].Cl>O>[CH3:21][S:22][C:23]1[NH:25][C:1](=[O:11])[CH:2]=[C:3]([C:5]([OH:7])=[O:6])[N:24]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66951Diethyl oxalacetateHCID 752702-Methyl-2-thiopseudourea sulfate

Product 1

HCID 1354730056-Hydroxy-2-(methylthio)-4-pyrimidinecarboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Neat diethyl oxalacetate (23.5 g, 125 mmol) was added to a solution of sodium hydroxide (15 g, 0.375 mol, 3 eq) in water (150 mL), giving a yellow solution. Solid S-methylisothiourea sulfate (17.4 g, 62.5 mmol, 0.5 eq) was added to the stirred solution. The mixture was stirred 15 hours. Concentrated HCl (40 mL, 0.48 mol) was added bringing the pH to 1, the resultant pale orange-pink suspension was stirred vigorously for 2 hours then filtered. The filter cake was washed with water (100 mL), and dried under high vacuum to afford 2-methylsulfanyl-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid as an off-white solid. 1H NMR (500 MHz, DMSO-d6) □ 13.22 (br s, 1H), 6.60 (s, 1H), 3.37 (br s, 1H), 2.53 (s, 3H); ESI-MS m/z 186.9 (M+H)+.

Workup

  1. customgiving a yellow solution
  2. stirringthe resultant pale orange-pink suspension was stirred vigorously for 2 hours
  3. filtrationthen filtered
  4. washThe filter cake was washed with water (100 mL)
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-72d00958ca7a4a64a7aeba9f751d92d5
Source dataset
uspto-grants-2014_09
Patent number
US08822451B2

Linked notes

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