Sodium hydride → Tert-butyl (e)-3-{8-[2-(4-isopropyl-1,3-thiazol-2-yl)ethyl]-4-oxo-4h-pyrido[1,2-a]pyrimidin-3-yl}-2-methyl-2-propenoate

HRID 1828518Notes

Reaction equation

HRID 1828518 reaction equation
C(OP([CH:9]([CH3:17])[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])(OCC)=O)C.[H-].[Na+].[CH:20]([C:23]1[N:24]=[C:25]([CH2:28][CH2:29][C:30]2[CH:42]=[CH:41][N:33]3[C:34](=[O:40])[C:35]([CH:38]=O)=[CH:36][N:37]=[C:32]3[CH:31]=2)[S:26][CH:27]=1)([CH3:22])[CH3:21].C(=O)([O-])O.[Na+]>O1CCCC1.C(OCC)(=O)C.C(O)(=O)C>[CH:20]([C:23]1[N:24]=[C:25]([CH2:28][CH2:29][C:30]2[CH:42]=[CH:41][N:33]3[C:34](=[O:40])[C:35](/[CH:38]=[C:9](\[CH3:17])/[C:10]([O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:11])=[CH:36][N:37]=[C:32]3[CH:31]=2)[S:26][CH:27]=1)([CH3:22])[CH3:21]

Participants

8

Reactant 4

HCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 11644679tert-Butyl 2-(diethoxyphosphoryl)propanoateHCID 220636238-(2-(4-isopropyl-1,3-thiazol-2-yl)-ethyl)-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carbaldehyde

Product 1

HCID 86588144Tert-butyl (e)-3-{8-[2-(4-isopropyl-1,3-thiazol-2-yl)ethyl]-4-oxo-4h-pyrido[1,2-a]pyrimidin-3-yl}-2-methyl-2-propenoateYield 93.1%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl 2-(diethylphosphono)propionate (70 mg) was dissolved in tetrahydrofuran(5 ml), added with sodium hydride (60% in oil, 40 mg), and stirred for 10 minutes. The reaction mixture was added with 8-(2-(4-isopropyl-1,3-thiazol-2-yl)-ethyl)-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carbaldehyde (56 mg), stirred for 10 minutes and added with acetic acid (0.2 ml), and then distributed between ethyl acetate and saturated aqueous sodium hydrogencarbonate. The organic layer was concentrated, and the residue was purified by silica gel column chromatography to obtain the title compound (70 mg) as yellow oil.

Workup

  1. stirringstirred for 10 minutes
  2. concentrationThe organic layer was concentrated
  3. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-fa0b047712a24136bae32803ed3e163a
Source dataset
uspto-grants-2006_06
Patent number
US07056917B2

Reaction notes

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