Potassium Carbonate → HCID 178490820、化合物

HRID 1976567ノート

反応式

HRID 1976567 の反応式
[ClH:1].[NH2:2][C:3]1[N:11]=[CH:10][N:9]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([OH:21])[CH:14]=2)[C:8]2[C:4]=1[N:5]=[C:6]([CH:22]([CH3:24])[CH3:23])[N:7]=2.C(=O)([O-])[O-].[K+].[K+].Br[C@H:32]1[CH2:36][CH2:35][C@H:34]([OH:37])[CH2:33]1.BrC1CCC(O)C1>CN(C=O)C>[ClH:1].[NH2:2][C:3]1[N:11]=[CH:10][N:9]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH:32]3[CH2:36][CH2:35][CH:34]([OH:37])[CH2:33]3)[CH:14]=2)[C:8]2[C:4]=1[N:5]=[C:6]([CH:22]([CH3:24])[CH3:23])[N:7]=2

参加物

6

反応物 4

HCID 11430Potassium Carbonate2 回HCID 123481943-Bromocyclopentan-1-olHCID 86756682HCID 86756682、化合物HCID 178490823HCID 178490823、化合物

生成物 1

HCID 178490820HCID 178490820、化合物収率 18.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of 6-amino-3-(3-hydroxy-4-methoxy-benzyl)-8-isopropyl-3H-purine hydrochloride (2.45 g, 7.0 mmole) in DMF (25 ml) was treated with potassium carbonate (5.80 g, 42 mmol), the mixture stirred at room temperature for 1 hour, then crude cis/trans-3-bromocyclopentanol (3.47 g, 21 mmole) was added. After 21 hours a second batch of potassium carbonate (2.90 g, 21 mmole) and 3-bromocyclopentanol (3.47 g, 21 mmole) were added. After stirring for 6 days the solid was filtered off and the solvent evaporated to dryness in vacuo. The residue was dissolved in chloroform (50 ml), extracted with IM NaOH solution and again evaporated in vacuo. The residue (5.84 g) was dissolved in dichloromethane:methanol, 98:2 (50 ml) and purified by column chromatography on silicagel, eluting with a gradient of 2-10% of methanol in dichloromethane. The fractions were collected (0.78 g; 28.0%), converted to the HCl salt and crystallized from acetone to give the title compound, (0.55 g, 18.1%), mp 185-187° C.

後処理

  1. stirringAfter stirring for 6 days the solid
  2. filtrationwas filtered off
  3. customthe solvent evaporated to dryness in vacuo
  4. dissolutionThe residue was dissolved in chloroform (50 ml)
  5. extractionextracted with IM NaOH solution
  6. customagain evaporated in vacuo
  7. dissolutionThe residue (5.84 g) was dissolved in dichloromethane
  8. custommethanol, 98:2 (50 ml) and purified by column chromatography on silicagel
  9. washeluting with a gradient of 2-10% of methanol in dichloromethane
  10. customThe fractions were collected (0.78 g; 28.0%)
  11. customcrystallized from acetone

出典と根拠

ORDレコード
ord-3b8045a0674d402d8bcc8ab14334fe81
出典データセット
uspto-grants-2001_05
特許番号
US06228859B1

反応ノート

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