HCID 90402755, compound → HCID 90402655, compound

HRID 2200702Notes

Reaction equation

HRID 2200702 reaction equation
[Cl:1][C:2]1[CH:40]=[CH:39][C:5]([CH2:6][N:7]2[C:15]3[C:14](=[O:16])[N:13]([CH2:17][CH2:18][CH2:19][O:20]C4CCCCO4)[C:12](=[O:27])[N:11]([CH3:28])[C:10]=3[N:9]=[C:8]2[O:29][CH2:30][CH2:31][O:32][CH:33]2[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]2)=[CH:4][CH:3]=1>Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:15]3[C:14](=[O:16])[N:13]([CH2:17][CH2:18][CH2:19][OH:20])[C:12](=[O:27])[N:11]([CH3:28])[C:10]=3[N:9]=[C:8]2[O:29][CH2:30][CH2:31][O:32][CH:33]2[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38]2)=[CH:39][CH:40]=1

Participants

3

Reactant 1

HCID 90402755HCID 90402755, compound

Product 1

HCID 90402655HCID 90402655, compoundYield 60.9%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 7-(4-chlorobenzyl)-8-(2-(cyclohexyloxy)ethoxy)-3-methyl-1-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)-1H-purine-2,6(3H,7H)-dione (123 mg, 0.214 mmol) in 1 mM ethanolic HCl (2 mL) was stirred at room temperature for 30 min. The reaction was concentrated to dryness to give a crude product, which was purified by preparative HPLC to give 7-(4-chlorobenzyl)-8-(2-(cyclohexyloxy)ethoxy)-1-(3-hydroxypropyl)-3-methyl-1H-purine-2,6(3H,7H)-dione (64 mg, 60.9% yield) as a white solid. 1H-NMR (CDCl3) δ 7.41-7.44 (d, 2H), 7.28-7.31 (d, 2H), 5.26 (s, 2H), 4.63-4.65 (m, 2H), 4.17-4.20 (t, 2H), 3.81-3.84 (m, 2H), 3.68-3.70 (br, 1H), 3.21 (m, 5H), 3.30-3.34 (m, 1H), 1.87-1.93 (m, 4H), 1.75-1.77 (t, 2H), 1.55-1.58 (m, 1H), 1.23-1.36 (m, 5H). LCMS retention time 2.893 min; LCMS MH+ 491.

Workup

  1. concentrationThe reaction was concentrated to dryness
  2. customto give a crude product, which
  3. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-a9b809f1416748c784e274579df9be99
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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