8-(4-Hydroxy-2,6-dioxa-tricyclo[3.3.1.03,7]non-1-yl)-1,3-dipropyl-7-(tetrahydro-pyran-2-yl)-3,7-dihydro-purine-2,6-dione → 8-(4-Hydroxy-2,6-dioxa-tricyclo [3.3.1.03.7]non-1-yl)-1,3-dipropyl-3,7-dihydro-purine-2,6-dione

HRID 480105Notes

Reaction equation

HRID 480105 reaction equation
[OH:1][CH:2]1[CH:9]2[CH2:10][C:5]3([C:11]4[N:19](C5CCCCO5)[C:18]5[C:17](=[O:26])[N:16]([CH2:27][CH2:28][CH3:29])[C:15](=[O:30])[N:14]([CH2:31][CH2:32][CH3:33])[C:13]=5[N:12]=4)[CH2:6][CH:7]([O:8]2)[CH:3]1[O:4]3>Cl.C1COCC1.CO>[OH:1][CH:2]1[CH:9]2[CH2:10][C:5]3([C:11]4[NH:19][C:18]5[C:17](=[O:26])[N:16]([CH2:27][CH2:28][CH3:29])[C:15](=[O:30])[N:14]([CH2:31][CH2:32][CH3:33])[C:13]=5[N:12]=4)[CH2:6][CH:7]([O:8]2)[CH:3]1[O:4]3

Participants

4

Reactant 1

HCID 187676568-(4-Hydroxy-2,6-dioxa-tricyclo[3.3.1.03,7]non-1-yl)-1,3-dipropyl-7-(tetrahydro-pyran-2-yl)-3,7-dihydro-purine-2,6-dione

Product 1

HCID 187676238-(4-Hydroxy-2,6-dioxa-tricyclo [3.3.1.03.7]non-1-yl)-1,3-dipropyl-3,7-dihydro-purine-2,6-dioneYield 38.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of 8-(4-hydroxy-2,6-dioxa-tricyclo[3.3.1.03,7]non-1-yl)-1,3-dipropyl-7-(tetrahydro-pyran-2-yl)-3,7-dihydro-purine-2,6-dione (0.065 mmol, 0.030 g) in 1:1 THF/MeOH (6 ml) was added 1N HCl (3 drops). The reaction was stirred at room temperature 4 h and then concentrated to dryness. The residue was purified by reverse phase HPLC, providing product (0.0094 g, 38%). 1H NMR (400 MHz, d6-DMSO): 0.80-0.89 (m, 6H), 1.48-1.56 (m, 2H), 1.60-1.70 (m, 2H), 1.9-2.09 (m, 2H), 2.2-2.25 (m, 1H), 3.78-3.82 (m, 2H), 3.89-3.91 (m, 2H), 3.99 (s, 1H), 4.21 (br s, 1H), 4.51 (br s, 1H), 4.80 (m, 1H).

Workup

  1. concentrationconcentrated to dryness
  2. customThe residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-3a98692ac3d24416af037009f5c824e0
Source dataset
uspto-grants-2003_11
Patent number
US06649600B1

Reaction notes

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