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

HRID 334135ノート

反応式

HRID 334135 の反応式
[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

参加物

7

反応物 3

HCID 10796Cesium carbonate2 回HCID 95576Methyl 2-bromopropionate2 回HCID 178458928HCID 178458928、化合物

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
50 °C

実験手順

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)

後処理

  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

出典と根拠

ORDレコード
ord-0c08b3e9d54b48609cfe3d27611a76ec
出典データセット
uspto-grants-2014_11
特許番号
US08883799B2

反応ノート

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