Thionyl Chloride → 4-Chloro-5-ethyl-6-methylthieno[2,3-d]pyrimidine

HRID 2408972ノート

反応式

HRID 2408972 の反応式
[CH3:1][CH2:2][C:3]1[C:7]2[C:8]([NH:10][CH:11]=[N:12][C:6]=2[S:5][C:4]=1[CH3:13])=O.S(Cl)([Cl:16])=O>CN(C=O)C>[Cl:16][C:8]1[C:7]2[C:3]([CH2:2][CH3:1])=[C:4]([CH3:13])[S:5][C:6]=2[N:12]=[CH:11][N:10]=1

参加物

4

反応物 2

HCID 24386Thionyl ChlorideHCID 230055345-Ethyl-6-methylthieno[2,3-d]pyrimidin-4(3H)-one

生成物 1

HCID 280648204-Chloro-5-ethyl-6-methylthieno[2,3-d]pyrimidine収率 73%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 5-ethyl-6-methyl-3-hydrothiopheno[2,3-d]pyrimidin-4-one (0.5 g), thionyl chloride (5 mL) and catalytic amount of DMF (0.2 mL) was refluxed for 1 h. Solvents were removed under vacuum and the mixture was diluted with ice cold water and stirred for 10 min. The solution was extracted with chloroform (3×100 mL) and the combined chloroform layer was washed with water, brine and dried over sodium sulfate. The solution was filtered and evaporated the solvent. The residue was triturated with hexane to give the product as a dark brown color solid (400 mg, 73%), mp 52-56° C. 1H NMR (400 MHz, CDCl3): δ 8.73 (1H, s), 3.05 (2H, q, J=7.5 Hz), 2.55 (3H, s), 1.24 (3H, t, J=7.6 Hz).

後処理

  1. temperaturewas refluxed for 1 h
  2. customSolvents were removed under vacuum
  3. additionthe mixture was diluted with ice cold water
  4. extractionThe solution was extracted with chloroform (3×100 mL)
  5. washthe combined chloroform layer was washed with water, brine
  6. dry with materialdried over sodium sulfate
  7. filtrationThe solution was filtered
  8. customevaporated the solvent
  9. customThe residue was triturated with hexane

出典と根拠

ORDレコード
ord-01577730153149adb1ab8b937889355d
出典データセット
uspto-grants-2014_08
特許番号
US08815879B2

反応ノート

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