Hydrochloric Acid → Methyl 3-pyrimidin-5-ylprop-2-enoate

HRID 2228911Notes

Reaction equation

HRID 2228911 reaction equation
[N:1]1[CH:6]=[C:5]([CH:7]=[CH:8][C:9]([OH:11])=[O:10])[CH:4]=[N:3][CH:2]=1.[CH3:12]O.Cl>O1CCOCC1>[N:1]1[CH:6]=[C:5]([CH:7]=[CH:8][C:9]([O:11][CH3:12])=[O:10])[CH:4]=[N:3][CH:2]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 534018453-(5-Pyrimidyl)acrylic acid

Product 1

HCID 53395016Methyl 3-pyrimidin-5-ylprop-2-enoate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

3-(5-Pyrimidyl)acrylic acid (100 g) was added to a mixture of dry methanol (2 L) and 4M hydrogen chloride in dioxan (445 ml) and allowed to stir at 60° C. under argon for 18 h. The mixture was cooled, and the solvent removed under reduced pressure. The residue was partitioned between dichloromethane (500 ml) and was washed with saturated sodium bicarbonate (300 ml). The aqueous layer was extracted with dichloromrethane and the combined dichloromethane layers were dried over magnesium sulfate and evaporated in vacuo to give methyl 3-(5-pyrimidinyl)acrylate (85 g). 1H-NMR (d6-DMSO) δ 3.82(3H, s), 7.03(1H, d), 7.75(1H, d) and 9.28(3H, s).

Workup

  1. temperatureThe mixture was cooled
  2. customthe solvent removed under reduced pressure
  3. customThe residue was partitioned between dichloromethane (500 ml)
  4. washwas washed with saturated sodium bicarbonate (300 ml)
  5. extractionThe aqueous layer was extracted with dichloromrethane
  6. dry with materialthe combined dichloromethane layers were dried over magnesium sulfate
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-298813e536fc4aaeacc3176b505b090b
Source dataset
uspto-grants-2002_07
Patent number
US06417192B1

Reaction notes

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