Cesium carbonate → methyl 2-(2-chloro-8-(2-hydroxypropan-2-yl)-6-morpholino-9H-purin-9-yl)propanoate

HRID 334135노트

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HRID 334135 반응식
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([C:11]([OH:14])([CH3:13])[CH3:12])[NH:8]2)=[C:4]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[N:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH:28]([CH3:33])[C:29]([O:31][CH3:32])=[O:30]>CN(C=O)C.O.C(OCC)(=O)C>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([C:11]([OH:14])([CH3:13])[CH3:12])[N:8]2[CH:28]([CH3:33])[C:29]([O:31][CH3:32])=[O:30])=[C:4]([N:15]2[CH2:16][CH2:17][O:18][CH2:19][CH2:20]2)[N:3]=1

참가 물질

7

반응물 3

HCID 10796Cesium carbonate2회HCID 95576Methyl 2-bromopropionate2회HCID 178458928HCID 178458928, 화합물

생성물 1

HCID 86667354methyl 2-(2-chloro-8-(2-hydroxypropan-2-yl)-6-morpholino-9H-purin-9-yl)propanoate수율 27.8%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
50 °C

실험 절차

2-(2-chloro-6-morpholino-9H-purin-8-yl)propan-2-ol (4.6 g, 15 mmol) was dissolved in DMF (16 mL), treated with cesium carbonate (10 g, 31 mmol) and methyl 2-bromopropanoate (7.6 g, 46 mmol), and heated at 50° C. for 3 hr. Partial conversion prompted addition of cesium carbonate (10 g, 31 mmol) and methyl 2-bromopropanoate (7.6 g, 46 mmol) and the reaction mixture was heated at 50° C. for 20 hr. The reaction mixture was cooled to ambient temperature and diluted with water and ethyl acetate and the layers separated. The aqueous phase was extracted into ethyl acetate (3×), dried over sodium sulfate, filtered, and absorbed onto celite for purification by flash chromatography to afford methyl 2-(2-chloro-8-(2-hydroxypropan-2-yl)-6-morpholino-9H-purin-9-yl)propanoate as a yellow foam (1.6 g, 26%). LC/MS (ESI+): m/z 384 (M+H)

후처리

  1. temperaturethe reaction mixture was heated at 50° C. for 20 hr
  2. temperatureThe reaction mixture was cooled to ambient temperature
  3. customthe layers separated
  4. extractionThe aqueous phase was extracted into ethyl acetate (3×)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customabsorbed onto celite for purification by flash chromatography

출처 및 근거

ORD 기록
ord-0c08b3e9d54b48609cfe3d27611a76ec
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08883799B2

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