2-Methyl-2-thiopseudourea sulfate → Tert-butyl 2-(methylthio)-5H-pyrrolo[3,4-D]pyrimidine-6(7H)-carboxylate

HRID 602960ノート

反応式

HRID 602960 の反応式
S(O)(O)(=O)=O.[CH3:6][S:7][C:8](=[NH:10])[NH2:9].[O-]CC.[Na+].CN([CH:18]=[C:19]1[C:23](=O)[CH2:22][N:21]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:20]1)C>C(O)C>[CH3:6][S:7][C:8]1[N:9]=[CH:18][C:19]2[CH2:20][N:21]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:22][C:23]=2[N:10]=1

参加物

5

反応物 3

HCID 752702-Methyl-2-thiopseudourea sulfate2 回HCID 2723922Sodium ethoxide2 回HCID 53415260tert-Butyl 3-[(dimethylamino)methylidene]-4-oxopyrrolidine-1-carboxylate

生成物 1

HCID 18442822Tert-butyl 2-(methylthio)-5H-pyrrolo[3,4-D]pyrimidine-6(7H)-carboxylate

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒2 回

反応条件

温度
80 °C

実験手順

To a solution of 2-methyl-2-thiopseudourea sulfate (3.5 g, 25 mmol) in ethanol at 0° C. was added a solution of sodium ethoxide (9.6 mL, 21%). After stirring for 10 min, a solution of tert-butyl 3-[(dimethylamino)methylene]-4-oxopyrrolidine-1-carboxylate (2.0 g, 8.32 mmol) in ethanol was added, and the mixture was heated at 80° C. for 1 h. Additional 2-methyl-2-thiopseudourea sulfate (3.5 g, 25 mmol) and sodium ethoxide (9.6 mL, 21%) was added and heated at 80° C. for 1 h. The ethanol was removed under reduced pressure, the residue was diluted with ethyl acetate (400 mL), washed with saturated aqueous sodium bicarbonate, brine, dried over sodium sulfate, and concentrated. The residue was purified on a Biotage silica gel cartridge (gradient 10-35% ethyl acetate in hexanes) to yield tert-butyl 2-(methylthio)-5,7-dihydro-6H-pyrrolo[3,4-d]pyrimidine-6-carboxylate.

後処理

  1. temperatureheated at 80° C. for 1 h
  2. customThe ethanol was removed under reduced pressure
  3. additionthe residue was diluted with ethyl acetate (400 mL)
  4. washwashed with saturated aqueous sodium bicarbonate, brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified on a Biotage silica gel cartridge (gradient 10-35% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-2fcde099a1d449219575aa90174e55d9
出典データセット
uspto-grants-2011_03
特許番号
US07906649B2

反応ノート

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