Benzene → HCID 136082964, compound

HRID 2165714Notes

Reaction equation

HRID 2165714 reaction equation
C(OC(OCC)C[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(OCC)(=O)C.C1C=CC=CC=1>CCO>[C:15]([NH:14][C:10]1[NH:11][C:12](=[O:13])[C:7]2[CH2:6][CH2:20][CH:19]([OH:21])[N:18]([C:22](=[O:24])[CH3:23])[C:8]=2[N:9]=1)(=[O:17])[CH3:16]

Participants

6

Reactant 4

HCID 241BenzeneHCID 962WaterHCID 8857Ethyl AcetateHCID 136109365HCID 136109365, compound

Product 1

HCID 136082964HCID 136082964, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-(2-Acetylamino-4-diacetylamino-1,6-dihydro-6-oxo-5-pyrimidinyl)propionaldehyde diethyl acetal (25.0 g, 0.66 mol) was heated with 100 ml of water on a steam bath for 4 hours. The solution was filtered hot to remove an insoluble by-product, and the filtrates were spin evaporated in vacuo to a thick syrup. This syrup was successively dissolved in ethanol and then ethylacetate followed by spin evaporation each time to give a solid which was digested with ethyl acetate. The solids were collected and dried; yield, 15.1 g (76%), mp 199°-201° of a cream colored solid which was used without further purification. Recrystallization of a portion from 2-propanol gave the analytical sample, mp 202°-205°; TLC (C6H6 :EtOH/10:1): NMR (DMSO-d6) δ11.75 (br s, 1H, NH), 11.30 (br s, 1H, NH, W1/2=5 Hz), 6.15 (d, 1H, J=5.0 Hz, OH), 6.06 (m, 1H, J= 2.7 Hz when D2O exchange removed OH CH), 2.43 (s, 3H, CH3), 2.17 (s, 3H, CH3), 2.40-2.10 (m, 2H, pyrimidine-CH2), 2.02-1.42 (m, 2H, CH2CH2CH); 13C-FT nmr (DMSO-d6) ppm: 15.7, 23.9, 27.2, 72.8, 102.2, 147.2, 152.4, 160.4, 171.0, 173.4; MS m/e 266, 248.

Workup

  1. filtrationThe solution was filtered hot
  2. customto remove an insoluble by-product
  3. customthe filtrates were spin evaporated in vacuo to a thick syrup
  4. dissolutionThis syrup was successively dissolved in ethanol
  5. customethylacetate followed by spin evaporation each time
  6. customto give a solid which
  7. customThe solids were collected
  8. customdried
  9. customyield
  10. custom15.1 g (76%), mp 199°-201° of a cream colored solid which was used without further purification
  11. customRecrystallization of a portion from 2-propanol
  12. customgave the analytical sample, mp 202°-205°

Sources & evidence

ORD record
ord-a522009d6ce54380a0a2b075cc6e9115
Source dataset
uspto-grants-1990_07
Patent number
US04940713

Reaction notes

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