Sodium hydride → HCID 13435056, compound

HRID 1759570Notes

Reaction equation

HRID 1759570 reaction equation
[I-].[CH3:2][S+](C)(C)=O.[H-].[Na+].[CH3:9][O:10][C:11]([C:13]1[CH:14]=[CH:15][C:16]2[N:17]([CH:33]=1)[C:18](=[O:32])[C:19]([CH2:30][CH3:31])=[C:20](/[CH:22]=[CH:23]/[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[N:21]=2)=[O:12]>CN(C)C=O>[C:24]1(/[CH:23]=[CH:22]/[C:20]2[N:21]=[C:16]3[CH:15]=[CH:14][C:13]4([CH2:2][CH:33]4[N:17]3[C:18](=[O:32])[C:19]=2[CH2:30][CH3:31])[C:11]([O:10][CH3:9])=[O:12])[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 13435034HCID 13435034, compound

Product 1

HCID 13435056HCID 13435056, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Trimethyl-sulphoxonium iodide (0.7 g) was reacted with 50% sodium hydride (0.15 g) in dimethylformamide (30 ml) under stirring at room temperature for 1 hour, then a solution of 2-trans-(2-phenyl-ethenyl)-3-ethyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-7-carboxylic acid methyl ester, m.p. 214°-216° C., (0.82 g) in dimethyl-formamide (20 ml) was added. The mixture was allowed to react under stirring at room temperature for 3 hours, then it was diluted with ice water and filtered. Crystallization from acetone gave 2-trans-(2-phenyl-ethenyl)-3-ethyl-6,7-methylen-4-oxo-4H-pyrido[1,2-a]pyrimidine-7-carboxylic acid, methyl ester, m.p. 194°-195° C. (0.58 g), which was reacted with 1% KOH in 95% ethanol solution (11 ml) at reflux temperature for 15 minutes. After cooling the reaction mixture was acidified with acetic acid, concentrated in vacuo and diluted with ice water: the precipitate was filtered and washed with water until neutral. Crystallization from acetone gave 0.34 g of 2-trans-(2-phenyl-ethenyl)-3-ethyl-6,7-methylen-4-oxo-4H-pyrido[1,2]pyrimidine-7-carboxylic acid, m.p. 215°-216° C., NMR (CF3COOD) δ: 1.22(m) and 2.93(m)(6,7-CH2 protons), 1.36(t) (CH2CH3), 2.93(m)(CH2 --CH3), 5.51(d.d)(C-6proton), 7.01(d) (C-9 proton), 7.31(d)(Hβ vinyl proton), 7.63(b.s)(phenyl protons), 7.76(d)(Hα vinyl proton), 8.26(d)(C-8 proton). By proceeding analogously the following compounds were prepared:

Workup

  1. customto react
  2. stirringunder stirring at room temperature for 3 hours
  3. filtrationfiltered
  4. customCrystallization from acetone

Sources & evidence

ORD record
ord-7dc32cf169734e43820753185e3b53e3
Source dataset
uspto-grants-1982_07
Patent number
US04341780

Reaction notes

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