Hydrochloric Acid → HCID 90402797, compound

HRID 2200738Notes

Reaction equation

HRID 2200738 reaction equation
[Si]([O:8][CH2:9][CH2:10][CH2:11][N:12]1[C:20](=[O:21])[C:19]2[N:18]([CH2:22][C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=3)[C:17]([NH:30][CH2:31][CH2:32][CH3:33])=[N:16][C:15]=2[N:14]([CH3:34])[C:13]1=[O:35])(C(C)(C)C)(C)C.Cl>C(O)C>[ClH:29].[Cl:29][C:26]1[CH:25]=[CH:24][C:23]([CH2:22][N:18]2[C:19]3[C:20](=[O:21])[N:12]([CH2:11][CH2:10][CH2:9][OH:8])[C:13](=[O:35])[N:14]([CH3:34])[C:15]=3[N:16]=[C:17]2[NH:30][CH2:31][CH2:32][CH3:33])=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 1317357113-((tert-butyldimethylsilyl)oxy)propyl-7-(4-chlorobenzyl)-3-methyl-8-(propylamino)-1H-purine-2,6(3H,7H)-dione

Product 1

HCID 90402797HCID 90402797, compoundYield 202.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Step 2 1-(3-((tert-Butyldimethylsilyl)oxy)propyl-7-(4-chlorobenzyl)-3-methyl-8-(propylamino)-1H-purine-2,6(3H,7H)-dione (0.15 g, 0.29 mmol) was dissolved in ethanol (3 mL) and 6N aqueous HCl (0.5 mL) was added. The clear solution was stirred at room temperature for 1 h. The reaction solvent was removed under reduced pressure to give 7-(4-chlorobenzyl)-1-(3-hydroxypropyl)-3-methyl-8-(propylamino)-1H-purine-2,6(3H,7H)-dione hydrochloride (0.13 g, 100% yield) as a white foam. LCMS retention time=3.021 min and 99% purity, LCMS MH+ 406. 1H NMR (DMSO-d6) δ 7.31 (dd, 4H, J=8 Hz and 42 Hz), 6.15-6.48 (brd s, NH2 and HCl), 5.30 (s, 2H), 3.84 (t, 2H, J=8 Hz), 3.38 (t, 2H, J=8 Hz), 3.34 (s, 3H), 3.26 (t, 2H, J=8 Hz), 1.59-1.68 (m, 2H), 1.46-1.57 (m, 2H), 0.81 (s, 3H, J=8 Hz).

Workup

  1. customThe reaction solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-6fddcf4fe28a43ada5267c0fca417bf7
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

Loading…