Acetic Anhydride → 2-[Acetoxy-(2-methyl-pyrimidin-5-yl)-methyl]acrylic acid methyl ester

HRID 705987노트

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HRID 705987 반응식
[CH3:1][O:2][C:3](=[O:15])[C:4]([CH:6]([OH:14])[C:7]1[CH:8]=[N:9][C:10]([CH3:13])=[N:11][CH:12]=1)=[CH2:5].[C:16](OC(=O)C)(=[O:18])[CH3:17].C([O-])(O)=O.[Na+]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:1][O:2][C:3](=[O:15])[C:4]([CH:6]([O:14][C:16](=[O:18])[CH3:17])[C:7]1[CH:12]=[N:11][C:10]([CH3:13])=[N:9][CH:8]=1)=[CH2:5]

참가 물질

6

반응물 3

HCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 677753262-[Hydroxy-(2-methyl-pyrimidin-5-yl)-methyl]acrylic acid methyl ester

생성물 1

HCID 677734642-[Acetoxy-(2-methyl-pyrimidin-5-yl)-methyl]acrylic acid methyl ester수율 61.1%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

2-[Hydroxy-(2-methyl-pyrimidin-5-yl)-methyl]-acrylic acid methyl ester (1.58 g, 7.58 mmol, 1 eq) and 4-DMAP (0.4 eq, 370 mg) were dissolved in 30 ml of dry DCM under argon atmosphere. To the mixture, cooled at 0° C., was added acetic anhydride (1.5 eq, 1.07 ml) dropwise, during 2 minutes. The mixture was warmed-up to room temperature and was stirred overnight (16 hours). The mixture was then poured into 150 ml of NaHCO3 saturated water solution and organic substances were extracted with DCM (3 times, 150 ml of DCM was used in total). The gathered DCM layers were dried, the solvent was evaporated and obtained was 2-[acetoxy-(2-methyl-pyrimidin-5-yl)-methyl]-acrylic acid methyl ester (1.16 g, yield=61.1%, purity=90%) in form of orange transparent oil. MS: [M+H]+=251.25 1H NMR (300 MHz; CDCl3) δ/ppm 2.73 (s, 3H), 3.72 (s, 2H), 6.05 (s, 1H), 6.49 (s, 1H), 6.61 (s, 1H) 8.65 (s, 2H)

후처리

  1. temperatureThe mixture was warmed-up to room temperature
  2. extractionwere extracted with DCM (3 times, 150 ml of DCM was used in total)
  3. dry with materialThe gathered DCM layers were dried
  4. customthe solvent was evaporated
  5. customobtained

출처 및 근거

ORD 기록
ord-08540bb6db6548119ab2d396ab220ba3
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09174968B2

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