Triethyl 2-phosphonopropionate → HCID 86588145, compound

HRID 1828521Notes

Reaction equation

HRID 1828521 reaction equation
[CH3:1][CH2:2][O:3][C:4]([CH:6](P(OCC)(OCC)=O)[CH3:7])=[O:5].C([Li])CCC.[CH:21]([C:24]1[N:25]=[C:26]([CH2:29][CH2:30][C:31]2[CH:49]=[CH:48][N:34]3[C:35](=[O:47])[C:36]([CH:45]=O)=[C:37]([N:39]4[CH2:44][CH2:43][O:42][CH2:41][CH2:40]4)[N:38]=[C:33]3[CH:32]=2)[S:27][CH:28]=1)([CH3:23])[CH3:22]>O1CCCC1>[CH:21]([C:24]1[N:25]=[C:26]([CH2:29][CH2:30][C:31]2[CH:49]=[CH:48][N:34]3[C:35](=[O:47])[C:36](/[CH:45]=[C:6](\[CH3:7])/[C:4]([O:3][CH2:2][CH3:1])=[O:5])=[C:37]([N:39]4[CH2:44][CH2:43][O:42][CH2:41][CH2:40]4)[N:38]=[C:33]3[CH:32]=2)[S:27][CH:28]=1)([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 107155Triethyl 2-phosphonopropionateHCID 22063658HCID 22063658, compoundHCID 178418339Butyllithium

Product 1

HCID 86588145HCID 86588145, compoundYield 23.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under nitrogen atmosphere, triethyl 2-phosphonopropionate (155 mg, 0.65 mmol) was dissolved in tetrahydrofuran (2 ml), added with n-butyl lithium (1 M, 0.65 ml) at −78° C., and stirred at the same temperature for 20 minutes. The reaction mixture was added with a solution of 8-[2-(4-isopropyl-1,3-thiazol-2-yl)ethyl]-2-morpholino-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carbaldehyde (50 mg) dissolved in tetrahydrofuran (1 ml). The cooling bath was removed, and the reaction mixture was warmed to room temperature and stirred overnight at room temperature. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (14 mg).

Workup

  1. customThe cooling bath was removed
  2. stirringstirred overnight at room temperature
  3. additionThe reaction mixture was added with saturated aqueous sodium hydrogencarbonate
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-07196da2e29c418e9b1e28de66dce235
Source dataset
uspto-grants-2006_06
Patent number
US07056917B2

Reaction notes

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