Methanol → Ethyl 2,4-dioxo-4-(2-phenoxypyrimidin-5-yl)butanoate

HRID 2274503Notes

Reaction equation

HRID 2274503 reaction equation
[O:1]([C:8]1[N:13]=[CH:12][C:11]([C:14](=[O:16])[CH3:15])=[CH:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17](OCC)(=[O:23])[C:18]([O:20][CH2:21][CH3:22])=[O:19].C[O-].[Na+].CO>C(OCC)C>[O:23]=[C:17]([CH2:15][C:14](=[O:16])[C:11]1[CH:12]=[N:13][C:8]([O:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[N:9][CH:10]=1)[C:18]([O:20][CH2:21][CH3:22])=[O:19]

Participants

6

Reactant 4

HCID 887MethanolHCID 7268Diethyl OxalateHCID 10942334Sodium MethoxideHCID 592524401-(2-Phenoxypyrimidin-5-yl)ethanone

Product 1

HCID 117993740Ethyl 2,4-dioxo-4-(2-phenoxypyrimidin-5-yl)butanoate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture consisting of 1-(2-phenoxypyrimidin-5-yl)ethanone (Example 38, Step B, 214 mg, 1.00 mmol) and diethyl oxalate (0.14 mL, 150 mg, 1.0 mmol) in diethyl ether (10 mL) under a nitrogen atmosphere at room temperature was stirred for ten minutes. Sodium methoxide (65 mg, 1.2 mmol) was subsequently added followed by methanol (1.0 mL). The solution was stirred overnight at room temperature. The off-white precipitate which had formed was collected by filtration and washed with diethyl ether. The solid was dissolved in water and the pH adjusted to 3 using acetic acid. The solid precipitate which formed was filtered and washed with water. The solid was air dried to afford a mixture comprising both the ethyl and methyl esters.

Workup

  1. stirringThe solution was stirred overnight at room temperature
  2. customThe off-white precipitate which had formed
  3. filtrationwas collected by filtration
  4. washwashed with diethyl ether
  5. dissolutionThe solid was dissolved in water
  6. customThe solid precipitate which formed
  7. filtrationwas filtered
  8. washwashed with water
  9. customdried
  10. customto afford a mixture

Sources & evidence

ORD record
ord-d334979c461548df805cf754c7c1fb07
Source dataset
uspto-grants-2015_09
Patent number
US09126973B2

Reaction notes

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