Sodium hydride → HCID 13435061, compound

HRID 1759571Notes

Reaction equation

HRID 1759571 reaction equation
[I-].[CH3:2][S+](C)(C)=O.[H-].[Na+].[CH3:9][O:10][C:11]1[CH:12]=[C:13](/[CH:17]=[CH:18]/[C:19]2[N:20]=[C:21]3[CH:31]=[CH:30][C:29]([C:32]([O:34][CH3:35])=[O:33])=[CH:28][N:22]3[C:23](=[O:27])[C:24]=2[CH2:25][CH3:26])[CH:14]=[CH:15][CH:16]=1>CN(C)C=O>[CH3:9][O:10][C:11]1[CH:12]=[C:13](/[CH:17]=[CH:18]/[C:19]2[N:20]=[C:21]3[CH:31]=[CH:30][C:29]4([CH2:2][CH:28]4[N:22]3[C:23](=[O:27])[C:24]=2[CH2:25][CH3:26])[C:32]([O:34][CH3:35])=[O:33])[CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 13435039HCID 13435039, compound

Product 1

HCID 13435061HCID 13435061, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Trimethyl-sulphoxonium iodide (1 g) was reacted with 50% sodium hydride (0.22 g) in dimethylformamide (30 ml) under stirring at room temperature for 30 minutes, then a solution of 2-trans-[2-(3-methoxy-phenyl)-ethenyl]-3-ethyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-7-carboxylic acid, methyl ester, m.p. 177°-179° C., (1.27 g) in dimethylformamide (20 ml) was added. The mixture was allowed to react under stirring at room temperature for 2 hours, then it was diluted with ice water and the precipitate was filtered, so obtaining 1.19 g of 2-trans-[2-(3-methoxy-phenyl)-ethenyl]-3-ethyl-6,7-methylen-4-oxo-4H-pyrido[1,2-a]pyrimidine-7-carboxylic acid, methyl ester (m.p. 184°-188° C.), which was treated with 0.5% KOH in 95% ethanol solution (40 ml) at reflux temperature for 15 minutes. After cooling the reaction mixture was diluted with water and acidified with acetic acid and the precipitate was filtered: crystallization from CH 2 Cl2 /methanol gave 2-trans-[2-(3-methoxy-phenyl)-ethenyl]-3-ethyl-6,7-methylen-4-oxo-4H-pyrido[1,2-a]pyrimidine-7-carboxylic acid (0.65 g), m.p. 184°-188° C. NMR (CF3COOD) δ: 1.22(d.d) (one of 6,7-methylen protons), 1.36(t) (--CH2 --CH3), 2,96(m)(--CH2CH3 and 6,7-methylen proton), 4.12(s) (OCH3), 5.50(d.d) (c-6 proton), 7.03(d) (c-9 proton), 7.36(d) (Hβ -vinyl proton), 7.68(d) (Hα -vinyl proton), 7.18-7.70(m) (4-phenyl protons), 8.26(d) (c-8 proton), JHαHβ =16 Hz.

Workup

  1. customto react
  2. stirringunder stirring at room temperature for 2 hours
  3. filtrationthe precipitate was filtered

Sources & evidence

ORD record
ord-63579cd3e8444a7a886a7a6280891427
Source dataset
uspto-grants-1982_07
Patent number
US04341780

Reaction notes

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