Methyl Acrylate → 2-[Hydroxy-(2-methyl-pyrimidin-5-yl)-methyl]acrylic acid methyl ester

HRID 474750Notes

Reaction equation

HRID 474750 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]=[O:9])=[CH:4][N:3]=1.C1N2CCN(CC2)C1.[C:18]([O:22][CH3:23])(=[O:21])[CH:19]=[CH2:20]>O1CCOCC1.O.[Cl-].[Na+].O>[CH3:23][O:22][C:18](=[O:21])[C:19]([CH:8]([OH:9])[C:5]1[CH:4]=[N:3][C:2]([CH3:1])=[N:7][CH:6]=1)=[CH2:20]

Participants

7

Reactant 3

HCID 7294Methyl AcrylateHCID 9237DabcoHCID 31609702-Methylpyrimidine-5-carbaldehyde

Product 1

HCID 677753262-[Hydroxy-(2-methyl-pyrimidin-5-yl)-methyl]acrylic acid methyl esterYield 83.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 312751,4-DioxaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of 2-methylpyrimidine-5-carbaldehyde (1 g, 8.18 mmol, 1 eq), DABCO (1 eq, 935 mg) and methyl acrylate (5 eq, 3.68 ml) dissolved in a 1,4-dioxane (40 ml/H2O (40 ml) mixture was stirred at room temperature for 2 hours. The mixture was then poured into 300 ml of brine and the organic substances were extracted with DCM (3 times, 300 ml was used in total). The gathered DCM layers were dried, the solvent was evaporated and the obtained crude oil was triturated with diethyl ether to afford 2-[hydroxy-(2-methyl-pyrimidin-5-yl)-methyl]acrylic acid methyl ester (1.58 g, yield=83.40%, purity=90%) in form of white powder. MS: [M+H]+=209.18 1H NMR (300 MHz; CDCl3) δ/ppm 2.72 (s, 3H), 3.61 (br.s., 1H), 3.75 (s, 3H), 5.58 (s, 1H), 5.97 (s, 1H), 6.43 (s, 1H) 8.64 (s, 2H)

Workup

  1. extractionthe organic substances were extracted with DCM (3 times, 300 ml was used in total)
  2. dry with materialThe gathered DCM layers were dried
  3. customthe solvent was evaporated
  4. customthe obtained crude oil
  5. customwas triturated with diethyl ether

Sources & evidence

ORD record
ord-88acd195df7c4acb9af65d0dec3faf64
Source dataset
uspto-grants-2014_01
Patent number
US08637536B2

Reaction notes

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