Morpholine → Tert-butyl 2-chloro-4-morpholino-5H-pyrrolo[3,4-D]pyrimidine-6(7H)-carboxylate

HRID 1626536노트

반응식

HRID 1626536 반응식
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[CH2:10][N:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:8][C:6]=2[N:7]=1.CCN(C(C)C)C(C)C.[NH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1.CCOC(C)=O>C(Cl)Cl.C([O-])(O)=O.[Na+]>[Cl:1][C:2]1[N:3]=[C:4]([N:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)[C:5]2[CH2:10][N:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:8][C:6]=2[N:7]=1

참가 물질

7

반응물 4

HCID 8083MorpholineHCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 17998715tert-Butyl 2,4-dichloro-5,7-dihydro-6H-pyrrolo(3,4-d)pyrimidine-6-carboxylate

생성물 1

HCID 71540665Tert-butyl 2-chloro-4-morpholino-5H-pyrrolo[3,4-D]pyrimidine-6(7H)-carboxylate

시약·촉매·용매 2

HCID 6344Dichloromethane용매2회HCID 516892Sodium Bicarbonate용매

실험 절차

To a solution of tert-butyl 2,4-dichloro-5H-pyrrolo[3,4-d]pyrimidine-6(7H)-carboxylate (1.00 g, 3.44 mmol) and DIPEA (0.672 mL, 3.86 mmol) at room temperature (20° C.) in DCM (7 mL) was added morpholine (0.33 mL, 3.86 mmol). After 2 h the reaction was diluted with DCM and Sat. NaHCO3. The organic layer was rinsed (brine), dried (anhydrous Na2SO4) and concentrated in vacuo. The desired product was isolated by flash chromatography (silica, 50 g, 0-50% EtOAc in petroleum ether (40-60) over 25 min) as a white solid (0.63 g, 1.85 mmol, 54% yield).

후처리

  1. washThe organic layer was rinsed (brine)
  2. dry with materialdried (anhydrous Na2SO4)
  3. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-f7a472d6d3d249cf9f7201607216f693
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08785457B2

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