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

HRID 44363

반응식

HRID 44363 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
100 °C

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-994adbae99914d29a183882d3a020cdd
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541421B2

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