Oxalic Acid → HCID 135577947, compound

HRID 2165720Notes

Reaction equation

HRID 2165720 reaction equation
C(O)(=O)C(O)=O.C(C(CC)C(O)=O)C.[C:15]([NH:18][C:19]1[NH:20][C:21](=[O:35])[C:22]([CH2:32][CH:33]=[O:34])=[C:23]([N:25]([C:29](=[O:31])[CH3:30])[C:26](=[O:28])[CH3:27])[N:24]=1)(=[O:17])[CH3:16].C(=O)(O)[O-].[Na+]>ClCCl>[C:15]([NH:18][C:19]1[NH:20][C:21](=[O:35])[C:22]([CH2:32][CH:33]=[O:34])=[C:23]([N:25]([C:29](=[O:31])[CH3:30])[C:26](=[O:28])[CH3:27])[N:24]=1)(=[O:17])[CH3:16]

Participants

5

Reactant 3

HCID 971Oxalic AcidHCID 516892Sodium BicarbonateHCID 136364561HCID 136364561, compound

Product 1

HCID 135577947HCID 135577947, compoundYield 46.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A slurry of Silica Gel 60 (6.0 g, Merck μ7734, 70-230 mesh) and aqueous oxalic acid (10%) (0.6 ml) in dichlormethane (12 ml) was stirred for 15 minutes. 2-(2-acetylamino-4-diacetylamino-1,6-dihydro-6-oxo-5-pyrimidinyl)acetaldehyde diethyl acetate (1.0 g, 2.7 mmol) was added and the mixture was stirred for 18 hours. Sodium bicarbonate (0.2 g, 2.4 mmol) was added and after 10 minutes the slurry was filtered and washed with ethyl acetate. The filtrates and wash were combined and spin evaporated in vacuo to give 0.37 g (46% of theory) of 2-(2-acetylamino-4-diacetylamino-1,6-dihydro-6-oxo-5-pyrimidinyl)acetaldehyde. The analytical sample was prepared by recrystallization from acetone to give 0.21 g (26% of theory), mp 169°-170° C.)

Workup

  1. filtrationwas filtered
  2. washwashed with ethyl acetate
  3. washThe filtrates and wash
  4. customspin evaporated in vacuo

Sources & evidence

ORD record
ord-a33e37df03444055a39b479029c025aa
Source dataset
uspto-grants-1990_07
Patent number
US04940713

Reaction notes

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