Tonapofylline → 8-[4-(3-Hydroxy-propyl)-bicyclo[2.2.2]oct-1-yl]-1,3-dipropyl-3,7-dihydro-purine-2,6-dione

HRID 480147Notes

Reaction equation

HRID 480147 reaction equation
[O:1]=[C:2]1[N:10]([CH2:11][CH2:12][CH3:13])[C:9]2[N:8]=[C:7]([C:14]34[CH2:21][CH2:20][C:17]([CH2:22][CH2:23][C:24](O)=[O:25])([CH2:18][CH2:19]3)[CH2:16][CH2:15]4)[NH:6][C:5]=2[C:4](=[O:27])[N:3]1[CH2:28][CH2:29][CH3:30]>C1COCC1.CO>[OH:25][CH2:24][CH2:23][CH2:22][C:17]12[CH2:16][CH2:15][C:14]([C:7]3[NH:6][C:5]4[C:4](=[O:27])[N:3]([CH2:28][CH2:29][CH3:30])[C:2](=[O:1])[N:10]([CH2:11][CH2:12][CH3:13])[C:9]=4[N:8]=3)([CH2:21][CH2:20]1)[CH2:19][CH2:18]2

Participants

4

Reactant 1

HCID 216466Tonapofylline

Product 1

HCID 187677268-[4-(3-Hydroxy-propyl)-bicyclo[2.2.2]oct-1-yl]-1,3-dipropyl-3,7-dihydro-purine-2,6-dioneYield 86%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-[4-(2,6-dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo-[2.2.2]oct-1-yl]-propionic acid (417 mg, 1.0 mmol) in THF (25 ml), cooled to 0° C. with the aid of an ice bath, was added BH3 (1.0 M in THF, 3.0 mmol). The resulting mixture was allowed to reach ambient temperature and stirred for a period of 60 h. Following the addition of MeOH (10 ml), the mixture was concentrated in vacuo to afford a white solid that was dissolved in MeOH (20 ml), stirred at rt for 2 h and evaporated to dryness in vacuo. The resulting white solid was recrystallized from EtOAc to afford 345 mg (86%) of a white powder. MS: 403 (MH+).

Workup

  1. customto reach ambient temperature
  2. concentrationthe mixture was concentrated in vacuo
  3. customto afford a white solid
  4. stirringstirred at rt for 2 h
  5. customevaporated to dryness in vacuo
  6. customThe resulting white solid was recrystallized from EtOAc

Sources & evidence

ORD record
ord-d3824cb15e5a482397fdafb1cdca1d5b
Source dataset
uspto-grants-2003_11
Patent number
US06649600B1

Reaction notes

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