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

HRID 602960노트

반응식

HRID 602960 반응식
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

참가 물질

5

반응물 3

HCID 752702-Methyl-2-thiopseudourea sulfate2회HCID 2723922Sodium ethoxide2회HCID 53415260tert-Butyl 3-[(dimethylamino)methylidene]-4-oxopyrrolidine-1-carboxylate

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매2회

반응 조건

온도
80 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-2fcde099a1d449219575aa90174e55d9
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07906649B2

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