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

HRID 1397175
ノート
印刷プレビュー

反応式

HRID 1397175 の反応式
[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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodide2 回HCID 14798Sodium HydroxideHCID 127555615-Acetyl-2-sulfanylidene-2,3-dihydropyrimidin-4(1H)-one

生成物 1

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

反応条件

温度
40 °C

実験手順

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].

後処理

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

出典と根拠

ORDレコード
ord-6da93fec866147979c9f0d25d4c67546
出典データセット
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08901147B2

反応ノート

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