Methyl iodide → 5,6-Dimethyl-2-(methylthio)thieno[2,3-d]pyrimidin-4-amine

HRID 44363

反応式

HRID 44363 の反応式
[C:1]([C:3]1[C:7]([CH3:8])=[C:6]([CH3:9])[S:5][C:4]=1[NH:10][C:11]([NH:13]C(=O)C1C=CC=CC=1)=[S:12])#[N:2].[OH-].[Na+].[CH3:24]I>C(O)C>[CH3:8][C:7]1[C:3]2[C:1]([NH2:2])=[N:13][C:11]([S:12][CH3:24])=[N:10][C:4]=2[S:5][C:6]=1[CH3:9]

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 899430N-benzoyl-N'-(3-cyano-4,5-dimethyl-2-thienyl)thiourea

生成物 1

HCID 12123385,6-Dimethyl-2-(methylthio)thieno[2,3-d]pyrimidin-4-amine収率 89%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
100 °C

実験手順

To a suspension of N-(3-cyano-4,5-dimethylthiophen-2-ylcarbamothioyl)-benzamide (Example 1a) (1.33 g, 4.22 mmol) in ethanol (25 mL) was added NaOH (2.0 N, 5.8 mL) at room temperature under nitrogen. After stirring at 100° C. under nitrogen for 0.5 h, the reaction mixture was cooled in an ice bath and MeI (0.8 mL) was added dropwise. After stirring for another 0.5 h, the resulting precipitate was collected by filtration, rinsed with water, 20% EtOH/H2O, and dried under vacuum to give the title compound (840 mg, 89%). 1H NMR (400 MHz, DMSO-d6) δ2.32 (s, 3H), 2.34 (s, 3H), 2.42 (s, 3H), 6.93 (bs, 2H). MS 226 (MH+).

後処理

  1. temperaturethe reaction mixture was cooled in an ice bath
  2. stirringAfter stirring for another 0.5 h
  3. filtrationthe resulting precipitate was collected by filtration
  4. washrinsed with water, 20% EtOH/H2O
  5. customdried under vacuum

出典と根拠

ORDレコード
ord-994adbae99914d29a183882d3a020cdd
出典データセット
uspto-grants-2013_09
特許番号
US08541421B2

関連ノート

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