Toluene → 5-Methyl-4-oxo-3,4,5,7-tetrahydro-pyrrolo[3,4-d]pyrimidine-6-carboxylic acid tert-butyl ester

HRID 450240

반응식

HRID 450240 반응식
[H-].[Na+].C(O[C:6](=O)[CH2:7][NH:8][C:9]([O:11]CC)=[O:10])C.C(O[C:18](=[O:22])[CH:19]=[CH:20][CH3:21])C.C(O)(=O)C.[CH:27]([NH2:29])=[NH:28].[O-]CC.[Na+].[C:34]1([CH3:40])[CH:39]=CC=C[CH:35]=1>C(O)C>[C:34]([O:11][C:9]([N:8]1[CH:20]([CH3:21])[C:19]2[C:18](=[O:22])[NH:29][CH:27]=[N:28][C:6]=2[CH2:7]1)=[O:10])([CH3:35])([CH3:39])[CH3:40]

참가 물질

8

반응물 6

HCID 1140TolueneHCID 121912-Butenoic acid, ethyl esterHCID 24758Sodium hydrideHCID 160693Formamidine acetateHCID 226277Ethyl 2-(ethoxycarbonylamino)acetateHCID 2723922Sodium ethoxide

생성물 1

HCID 1361587835-Methyl-4-oxo-3,4,5,7-tetrahydro-pyrrolo[3,4-d]pyrimidine-6-carboxylic acid tert-butyl ester

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a suspension of NaH (9.72 g, 243 mmol, 60% in mineral oil) in toluene (100 mL), ethoxycarbonylamino-acetic acid ethyl ester (38 g, 187 mmol) is added at 0° C. The reaction is left stirring for 5 h at the same temperature. At that point but-2-enoic acid ethyl ester (25.6 g, 224 mmol) is added and the reaction allowed to warm up to rt and stirred for further 2 h. Ethanol (30 mL) is added and the reaction is then evaporated. The crude 1-tert-butyl 3-ethyl 2-methyl-4-oxopyrrolidine-1,3-dicarboxylate is dissolved in EtOH (1500 mL), then formamidine acetate (343 g, 1189 mmol) is added followed by sodium ethoxide (47.2 g, 694 mmol). The reaction is left stirring at 90° C. for 8 h. The solvent is then removed and to the crude material a saturated solution of NH4Cl (200 mL) is added followed by DCM (1 L). The water layer is extracted two times with DCM. The organics are dried and evaporate. The crude product is separated by FCC (DCM/MeOH 100:0 to 90:10) to give the title compound. MS (ESI) m/z 252.2 (M+1).

후처리

  1. additionis added at 0° C
  2. waitThe reaction is left
  3. stirringstirred for further 2 h
  4. customthe reaction is then evaporated
  5. dissolutionThe crude 1-tert-butyl 3-ethyl 2-methyl-4-oxopyrrolidine-1,3-dicarboxylate is dissolved in EtOH (1500 mL)
  6. waitThe reaction is left
  7. stirringstirring at 90° C. for 8 h
  8. customThe solvent is then removed and to the crude material a saturated solution of NH4Cl (200 mL)
  9. additionis added
  10. extractionThe water layer is extracted two times with DCM
  11. customThe organics are dried
  12. customevaporate
  13. customThe crude product is separated by FCC (DCM/MeOH 100:0 to 90:10)

출처 및 근거

ORD 기록
ord-a32c48144a074d7ab6f70ae602b01c0d
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08486954B2

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