Water → HCID 136380620, compound

HRID 1828523Notes

Reaction equation

HRID 1828523 reaction equation
[CH3:1][CH2:2][O:3][C:4]([CH:6](P(OCC)(OCC)=O)[F:7])=[O:5].C([Li])CCC.[CH:21]([C:24]1[N:25]=[C:26]([CH2:29][CH2:30][C:31]2[CH:44]=[CH:43][N:34]3[C:35](=[O:42])[C:36]([CH:40]=O)=[C:37]([OH:39])[N:38]=[C:33]3[CH:32]=2)[S:27][CH:28]=1)([CH3:23])[CH3:22].O>O1CCCC1.CN(C)C=O>[F:7]/[C:6](=[CH:40]\[C:36]1[C:35](=[O:42])[N:34]2[CH:43]=[CH:44][C:31]([CH2:30][CH2:29][C:26]3[S:27][CH:28]=[C:24]([CH:21]([CH3:22])[CH3:23])[N:25]=3)=[CH:32][C:33]2=[N:38][C:37]=1[OH:39])/[C:4]([O:3][CH2:2][CH3:1])=[O:5]

Participants

7

Reactant 4

HCID 962WaterHCID 2734865Triethyl 2-fluoro-2-phosphonoacetateHCID 135724442HCID 135724442, compoundHCID 178418339Butyllithium

Product 1

HCID 136380620HCID 136380620, compoundYield 25.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

2-Fluoro-2-phosphonoacetic acid triethyl ester (384 mg) was dissolved in tetrahydrofuran (3ml) and dimethylformamide (1.5 ml), added with n-butyl lithium (1.6 M, 1 ml) at −78° C. under nitrogen atmosphere, and then the mixture was 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-hydroxy-4-oxo-4H-pyrido[1,2-a]-pyrimidine-3-carbaldehyde (108 mg) dissolved in tetrahydrofuran (2 ml). The reaction temperature was gradually raised to room temperature, and the reaction mixture was stirred overnight at the same temperature. The reaction mixture was added with water and extracted with methylene chloride, and the organic layer was dried over magnesium sulfate. Then, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (35 mg) as a mixture of (E)- and (Z)-isomers.

Workup

  1. stirringthe reaction mixture was stirred overnight at the same temperature
  2. extractionextracted with methylene chloride
  3. dry with materialthe organic layer was dried over magnesium sulfate
  4. customThen, the solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-88be8b1e55854adfb6cf3a59cb7eb386
Source dataset
uspto-grants-2006_06
Patent number
US07056917B2

Reaction notes

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