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Bromide ion → 2-Butoxy-9-(1-tert-butoxycarbonylpiperidin-4-ylmethyl)-8-methoxyadenine

HRID 2403788
ノート
印刷プレビュー

反応式

HRID 2403788 の反応式
C(=O)([O-])[O-].[K+].[K+].FC(F)(F)C(O)=O.[CH2:14]([O:18][C:19]1[N:27]=[C:26]2[C:22]([N:23]=[C:24]([O:28][CH3:29])[NH:25]2)=[C:21]([NH2:30])[N:20]=1)[CH2:15][CH2:16][CH3:17].Br[CH2:32][CH:33]1[CH2:38][CH2:37][N:36]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:35][CH2:34]1.[Br-]>CN(C)C=O.O>[NH2:30][C:21]1[N:20]=[C:19]([O:18][CH2:14][CH2:15][CH2:16][CH3:17])[N:27]=[C:26]2[C:22]=1[N:23]=[C:24]([O:28][CH3:29])[N:25]2[CH2:32][CH:33]1[CH2:38][CH2:37][N:36]([C:39]([O:41][C:42]([CH3:43])([CH3:45])[CH3:44])=[O:40])[CH2:35][CH2:34]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 259Bromide ionHCID 11430Potassium CarbonateHCID 15512811tert-Butyl 4-(bromomethyl)piperidine-1-carboxylateHCID 178450370HCID 178450370、化合物

生成物 1

HCID 583060912-Butoxy-9-(1-tert-butoxycarbonylpiperidin-4-ylmethyl)-8-methoxyadenine収率 94.1%

試薬・触媒・溶媒 2

HCID 962
Water
溶媒
HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
60 °C

実験手順

Potassium carbonate (650 mg) was added to a solution of 2-butoxy-8-methoxy-9H-purin-6-amine trifluoroacetate salt (550 mg) in dry N,N-dimethylformamide (5.5 ml) and the reaction mixture heated at 60° C. for 1 hour. 1,1-Dimethylethyl 4-(bromomethyl)-1-piperidinecarboxylate (500 mg) was added using additional DMF (1.5 ml) to transfer the residual bromide and the reaction mixture stirred at 50° C. for 3 hours. After 16 hours at room temperature, heating at 50° C. was continued for another 5 hours to complete the reaction. Water was added and the reaction mixture extracted three times with ethyl acetate. The combined organic extracts were washed with water, dried over anhydrous sodium sulfate, filtered, concentrated and dried under high vacuum. Purification by chromatography on silica gel eluting with a gradient of 1-2.5% methanol in chloroform afforded the title compound as yellow solid (640 mg).

後処理

  1. waitAfter 16 hours at room temperature
  2. temperatureheating at 50° C.
  3. waitwas continued for another 5 hours
  4. customthe reaction
  5. extractionthe reaction mixture extracted three times with ethyl acetate
  6. washThe combined organic extracts were washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customdried under high vacuum
  11. customPurification by chromatography on silica gel eluting with a gradient of 1-2.5% methanol in chloroform

出典と根拠

ORDレコード
ord-e6f4612d8b29448b9741823eb32b5dce
出典データセット
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08802684B2

反応ノート

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