Hydrochloric Acid → HCID 90402447, compound

HRID 2200650Notes

Reaction equation

HRID 2200650 reaction equation
[Si]([O:8][CH2:9][CH:10]([O:44][CH3:45])[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]([O:30][C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([O:37][C:38]([F:41])([F:40])[F:39])[CH:32]=3)=[N:16][C:15]=2[N:14]([CH3:42])[C:13]1=[O:43])(C(C)(C)C)(C)C.Cl>C(O)C>[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][CH:10]([O:44][CH3:45])[CH2:9][OH:8])[C:13](=[O:43])[N:14]([CH3:42])[C:15]=3[N:16]=[C:17]2[O:30][C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([O:37][C:38]([F:41])([F:39])[F:40])[CH:32]=2)=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 90403033HCID 90403033, compound

Product 1

HCID 90402447HCID 90402447, compoundYield 16.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1-(3-(tert-butyldimethylsilyloxy)-2-methoxypropyl)-7-(4-chlorobenzyl)-3-methyl-8-(3-(trifluoromethoxy)phenoxy)-1H-purine-2,6(3H,7H)-dione (150 mg, 0.22 mmol) in ethyl alcohol (5 mL) was added concentrated HCl (0.1 mL). The reaction was stirred for 10 minutes. Then it was concentrated and purified by preparative HPLC to give 7-(4-chlorobenzyl)-1-(3-hydroxy-2-methoxypropyl)-3-methyl-8-(3-(trifluoromethoxy)phenoxy)-1H-purine-2,6(3H,7H)-dione (18 mg, 16.2% yield) as white solid. 1H-NMR (DMSO-d6) δ 7.63-7.59(t, 1H), 7.50(s, 1H), 7.45-7.43(m, 5H), 7.34-7.32(d, 1H), 5.44(s, 2H), 4.65-4.62(t, 1H), 4.12-4.08(q, 1H), 3.84-3.79(q, 1H), 3.53-3.41(m, 2H), 3.29-3.28(d, 6H). LCMS retention time 3.089 min; LCMS MH+ 555.

Workup

  1. concentrationThen it was concentrated
  2. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-a0780201d3d2453386fd60afe84f44d9
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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