5-Chloro-2(1H)-pyrimidinone → HCID 22823685, compound

HRID 1075143Notes

Reaction equation

HRID 1075143 reaction equation
[C:1]([NH:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:7][CH:6]1Cl)(=[O:3])[CH3:2].[K].[Cl:26][C:27]1[CH:28]=[N:29][C:30](=[O:33])[NH:31][CH:32]=1>CN(C)C=O>[C:1]([NH:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:7][CH:6]1[N:31]1[CH:32]=[C:27]([Cl:26])[CH:28]=[N:29][C:30]1=[O:33])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 1085785-Chloro-2(1H)-pyrimidinoneHCID 5462222PotassiumHCID 12903138HCID 12903138, compound

Product 1

HCID 22823685HCID 22823685, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

2-Desoxy-2-acetylamino-3,4,6-tri-O-actyl-D-glucopyranosylchloride (0.01 mol) and the potassium salt of 5-chloropyrimid-2-one (0.008 mol) were heated together in dimethylformamide (60 ml) with stirring at 80° C. for 24 hours. The solvent was then evaporated at reduced pressure (1 mm Hg) and the residue was extracted with chloroform (120 ml). The chloroform solution was washed with aqueous 1 N NaOH (2×3 ml) and water (3 ml) before drying (Mg SO4). Evaporation left the title compound which was further purified by trituration with ether and recrystallization from a small volume of methanol; yield 50%, m.p. 165°-167° C. when the sample is heated rapidly. (Found: C, 47.00; H, 4.82. Calc. for C18H22ClN3O9: : C, 47.02; H, 4.82)

Workup

  1. customThe solvent was then evaporated at reduced pressure (1 mm Hg)
  2. extractionthe residue was extracted with chloroform (120 ml)
  3. washThe chloroform solution was washed with aqueous 1 N NaOH (2×3 ml) and water (3 ml)
  4. dry with materialbefore drying (Mg SO4)
  5. customEvaporation
  6. waitleft the title compound which
  7. customwas further purified by trituration with ether and recrystallization from a small volume of methanol
  8. temperatureyield 50%, m.p. 165°-167° C. when the sample is heated rapidly

Sources & evidence

ORD record
ord-909a5763061042dbbd27d547e95ba664
Source dataset
uspto-grants-1983_07
Patent number
US04395406

Reaction notes

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