HCID 136109365, compound → HCID 135578121, compound

HRID 2165717Notes

Reaction equation

HRID 2165717 reaction equation
C([O:3][CH:4](OCC)[CH2:5][CH2:6][C:7]1[C:12](=[O:13])[NH:11][C:10]([NH:14][C:15](=[O:17])[CH3:16])=[N:9][C:8]=1[N:18]([C:22](=[O:24])[CH3:23])[C:19](=[O:21])[CH3:20])C>O>[C:15]([NH:14][C:10]1[NH:11][C:12](=[O:13])[C:7]([CH2:6][CH2:5][CH:4]=[O:3])=[C:8]([N:18]([C:22](=[O:24])[CH3:23])[C:19](=[O:21])[CH3:20])[N:9]=1)(=[O:17])[CH3:16]

Participants

3

Reactant 1

HCID 136109365HCID 136109365, compound

Product 1

HCID 135578121HCID 135578121, compoundYield 67.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 3-(2-acetylamino-4-diacetylamino-1,6-dihydro-6-oxo-5-pyrimidinyl)propionaldehyde diethyl acetal (30.0 g, 78.5 mmol) in distilled water (600 ml) was stirred at 53° C. for 3.5 hours and spin evaporated in vacuo at 45° C. The residue was dissolved in dichloromethane (750 ml), washed with brine (50 ml), dried (MgSO4), and spin evaporated in vacuo to a dry solid. Recrystallization from acetone gave 16.23 g (67% of theory) of 3-(2-acetylamino-4-diacetylamino-1,6-dihydro-6-oxo-5-pyrimidinyl)propionaldehyde, mp 164°-168° C., which was identical to that prepared by Method 1.

Workup

  1. customspin evaporated in vacuo at 45° C
  2. dissolutionThe residue was dissolved in dichloromethane (750 ml)
  3. washwashed with brine (50 ml)
  4. dry with materialdried (MgSO4)
  5. customspin evaporated in vacuo to a dry solid
  6. customRecrystallization from acetone

Sources & evidence

ORD record
ord-b037b179fce54342839ad84e0ad0e545
Source dataset
uspto-grants-1990_07
Patent number
US04940713

Reaction notes

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