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

HRID 474750

반응식

HRID 474750 반응식
[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]

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 312751,4-Dioxane용매HCID 57417360Sodium chloride; water용매

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-88acd195df7c4acb9af65d0dec3faf64
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637536B2

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