Sodium hydride → HCID 77976314, compound

HRID 1247941Notes

Reaction equation

HRID 1247941 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]1[CH2:24][CH2:23][C:22](=[CH:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:20]=1[N:21]=2)=[O:12]>CN(C)C=O.C(O)(=O)C>[CH3:9][O:10][C:11]([C:13]12[CH2:2][CH:33]1[N:17]1[C:18](=[O:32])[C:19]3[CH2:24][CH2:23][C:22](=[CH:25][C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)[C:20]=3[N:21]=[C:16]1[CH:15]=[CH:14]2)=[O:12]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 53937926HCID 53937926, compound

Product 1

HCID 77976314HCID 77976314, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent2×

Procedure

Trimethyl-sulphoxonium iodide (1.8 g) was reacted with 50% sodium hydride (0.39 g) in dimethyl formamide (30 ml) under stirring at room temperature for 60 minutes, then a solution of 3-benzylidene-1,2,3,10-tetrahydro-10-oxo-cyclopenta[d]pyrido[1,2-a]pyrimidine-7-carboxylic acid methyl ester, m.p. 248°-250° C., (2.49 g) in dimethylformamide (30 ml) was added. The mixture was allowed to react at room temperature for 1 hour then it was diluted with ice water and neutralized with acetic acid. The precipitate was filtered and washed with water to give 2.55 g of 3-benzylidene-7,8-methylene-1,2,3,10-tetrahydro-10-oxo-cyclopenta[d]pyrido[1,2-a]pyrimidine-7-carboxylic acid methyl ester, m.p. 185°-187° C., which was treated with 0.5% KOH in 95% ethanol solution (90 ml) at reflux temperature for 15 minutes. After cooling the reaction mixture was acidified with acetic acid and diluted with water: the precipitate was filtered, washed with water until neutral and crystallized from CH 2 Cl2 /methanol to give 1.8 g of 3-benzylidene-7,8-methylene-1,2,3,10-tetrahydro-10-oxo-cyclopenta[d]pyrido[1,2-a]pyrimidine-7-carboxylic acid, m.p. 230°-240° C. dec., NMR (CF3COOD) δ ppm: 1.19 (t) (1H, 7,8-methylene proton), 2.91 (d d) (1H, 7,8-methylene proton), 3.32 (br s) (4H, cyclopentane protons), 3.51 (d.d.) (1H, C-8 proton), 7.01 (d) (1H, C-5 proton), 7.45 (m) (1H, =CH--), 7.58 (br s) (5H, phenyl protons), 8.26 (d) (1H, C-6 proton).

Workup

  1. customto react at room temperature for 1 hour
  2. filtrationThe precipitate was filtered
  3. washwashed with water

Sources & evidence

ORD record
ord-488943cdba8a4707a3794f9e30a894c2
Source dataset
uspto-grants-1985_06
Patent number
US04521419

Reaction notes

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