Water → 2-Pyrimidineacetic acid ethyl ester

HRID 1741281Notes

Reaction equation

HRID 1741281 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[CH:7](C(OCC)=O)[C:8]([O:10][CH2:11][CH3:12])=[O:9].[Cl-].[Na+].O>CS(C)=O>[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

5

Reactant 3

HCID 962Water2×HCID 5234Sodium ChlorideHCID 2303274Diethyl (pyrimidin-2-yl)propanedioate

Product 1

HCID 123671052-Pyrimidineacetic acid ethyl esterYield 62.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of diethyl 2-(pyrimidin-2-yl)malonate (1.0 g, 4.2 mmol) and sodium chloride (491 mg, 8.4 mmol) in DMSO (6 ml) and water (151 μl, 8.4 mmol) was heated at 180° C. for 20 min. The mixture was cooled to room temperature, water (12 ml) was added, and the solution extracted with EtOAc (2×20 ml). The combined organic layers were dried (MgSO4) and evaporated. The residue was chromatographed on silica, eluting with hexane:EtOAc (2:1), to afford the ester (434 mg, 62%) as a pale yellow oil. 1H NMR (250 MHz, CDCl3) δ 1.27 (3H, t, J=7.1 Hz), 4.04 (2H, s), 4.23 (2H, q, J=7.1 Hz), 7.22 (1H, t, J=5.3 Hz), 8.72 (2H, d, J=5.3 Hz).

Workup

  1. extractionthe solution extracted with EtOAc (2×20 ml)
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. customevaporated
  4. customThe residue was chromatographed on silica
  5. washeluting with hexane:EtOAc (2:1)

Sources & evidence

ORD record
ord-5fba5d275e4a4021a30c9c720adf42f1
Source dataset
uspto-grants-1999_10
Patent number
US05973156

Reaction notes

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