Sodium hydride → HCID 118483096, compound

HRID 1773344Notes

Reaction equation

HRID 1773344 reaction equation
[Cl:1][C:2]1[NH:7][C:6](=[O:8])[C:5]([Cl:9])=[C:4]([Cl:10])[N:3]=1.[H-].[Na+].[CH3:13][O:14][C:15](=[O:18])[CH2:16]Br>CN(C=O)C.O>[CH3:13][O:14][C:15](=[O:18])[CH2:16][N:7]1[C:6](=[O:8])[C:5]([Cl:9])=[C:4]([Cl:10])[N:3]=[C:2]1[Cl:1]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 136034537HCID 136034537, compound

Product 1

HCID 118483096HCID 118483096, compoundYield 22.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,5,6-trichloro-3H-pyrimidin-4-one (20.0 g, 0.1 mol) in DMF (150 mL) was added NaH (60% in mineral oil, 6.0 g, 0.12 mol) in portions at 0° C. and the mixture was stirred for 30 min. Bromoacetic acid methyl ester (18.3 g, 0.12 mol) was then added, and the reaction mixture was stirred at RT overnight. The solution was diluted with water (800 mL) and extracted with EA (200 mL, 3×). The combined organics were washed with water (800 mL, 3×), washed with brine (500 mL), dried (Na2SO4) and concentrated. The residue was purified by silica chromatography (1:50, EA:PE) to give 6.0 g of the title product (22%). 1H NMR (400 MHz, CDCl3): δ 3.80 (s, 3H), 5.04 (s, 2H). [M+H] Calc'd for C7H5Cl3N2O3, 271. Found, 271.

Workup

  1. stirringthe reaction mixture was stirred at RT overnight
  2. extractionextracted with EA (200 mL, 3×)
  3. washThe combined organics were washed with water (800 mL, 3×)
  4. washwashed with brine (500 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe residue was purified by silica chromatography (1:50, EA:PE)

Sources & evidence

ORD record
ord-005a4ca33aa3494e89ffbc71a318cf65
Source dataset
uspto-grants-2016_02
Patent number
US09255097B2

Reaction notes

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