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Hydrochloric Acid → 5-acetyl-2-(methylthio)pyrimidin-4(3H)-one

HRID 1397175
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HRID 1397175 반응식
[C:1]([C:4]1[C:5](=[O:11])[NH:6][C:7](=[S:10])[NH:8][CH:9]=1)(=[O:3])[CH3:2].[OH-].[Na+].[CH3:14]I.Cl>>[C:1]([C:4]1[C:5](=[O:11])[NH:6][C:7]([S:10][CH3:14])=[N:8][CH:9]=1)(=[O:3])[CH3:2]
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참가 물질

5

반응물 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodide2회HCID 14798Sodium HydroxideHCID 127555615-Acetyl-2-sulfanylidene-2,3-dihydropyrimidin-4(1H)-one

생성물 1

HCID 566989835-acetyl-2-(methylthio)pyrimidin-4(3H)-one수율 69.1%

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온도
40 °C

실험 절차

5-Acetyl-2-thioxo-2,3-dihydropyrimidin-4(1H)-one (Ryan Scientific) (2.3 g, 13.51 mmol) was dissolved in NaOH (20.27 mL, 20.27 mmol), then MeI (0.894 mL, 14.30 mmol) was added to the reaction mixture while stifling. The reaction mixture was heated at 40° C. for 1.5 hours. Additional MeI (0.894 mL, 14.30 mmol) was added and the reaction was allowed to stir at rt for 18 hours. The reaction mixture was cooled with an ice-water bath, acidified to pH 6 with concentrated HCl solution, then the resulting precipitate was filtered to obtain 1.72 g of the desired product (69% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.49 (br. s., 6 H) 8.35 (s, 1 H) 13.40 (br. s., 1 H). MS (ES+): m/z=185.1 (100) [MH+]. HPLC: tR=1.0 minute over 3 minutes. Purity: >90% [HPLC (LC/MS) at 220 nm].

후처리

  1. temperatureThe reaction mixture was cooled with an ice-water bath
  2. filtrationthe resulting precipitate was filtered

출처 및 근거

ORD 기록
ord-6da93fec866147979c9f0d25d4c67546
출처 데이터셋
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08901147B2

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