Potassium Carbonate → HCID 178490820, compound

HRID 1976567Notes

Reaction equation

HRID 1976567 reaction equation
[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

Participants

6

Reactant 4

HCID 11430Potassium Carbonate2×HCID 123481943-Bromocyclopentan-1-olHCID 86756682HCID 86756682, compoundHCID 178490823HCID 178490823, compound

Product 1

HCID 178490820HCID 178490820, compoundYield 18.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-3b8045a0674d402d8bcc8ab14334fe81
Source dataset
uspto-grants-2001_05
Patent number
US06228859B1

Reaction notes

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