Water → HCID 90402497, compound

HRID 2200648Notes

Reaction equation

HRID 2200648 reaction equation
[Cl:1][C:2]1[CH:36]=[CH:35][C:5]([CH2:6][N:7]2[C:15]3[C:14](=[O:16])[N:13]([CH2:17][CH:18]4[CH2:20][O:19]4)[C:12](=[O:21])[N:11]([CH3:22])[C:10]=3[N:9]=[C:8]2[O:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26](OC(F)(F)F)[CH:25]=2)=[CH:4][CH:3]=1.C(O)([C:39]([F:42])([F:41])[F:40])=O.[OH2:44]>O1CCOCC1>[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][CH:18]([OH:44])[CH2:20][OH:19])[C:12](=[O:21])[N:11]([CH3:22])[C:10]=3[N:9]=[C:8]2[O:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([C:39]([F:42])([F:41])[F:40])[CH:25]=2)=[CH:35][CH:36]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 90403240HCID 90403240, compound

Product 1

HCID 90402497HCID 90402497, compoundYield 48.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 7-(4-chlorobenzyl)-3-methyl-1-(oxiran-2-ylmethyl)-8-(3-(trifluoromethoxy)phenoxy)-1H-purine-2,6(3H,7H)-dione (140 mg, 0.268 mmol) in 1,4-dioxane (10 mL) was added TFA (0.11 mL, 1.48 mmol) and water (2 mL); then the mixture was stirred at 80° C. for 2 h. The mixture was concentrated; then purified by silica gel chromatography eluting with DCM/methanol (50:1 to 20:1) to give 7-(4-chlorobenzyl)-1-(2,3-dihydroxypropyl)-3-methyl-8-(3-(trifluoromethyl)phenoxy)-1H-purine-2,6(3H,7H)-dione (70 mg, 48.4% yield) as white solid. 1H-NMR (DMSO-d6) δ 7.63-7.58(t, 1H), 7.48(s, 1H), 7.44-7.41(m, 5H), 7.34-7.31(d, 1H), 5.44(s, 2H), 4.68-4.67(d, 1H), 4.55-4.52(m, 1H), 4.01-3.98(m, 1H), 3.84-3.80(m, 2H), 3.33(s, 2H), 3.29(s, 3H). LCMS retention time 2.811 min; LCMS MH+ 541.

Workup

  1. concentrationThe mixture was concentrated
  2. customthen purified by silica gel chromatography
  3. washeluting with DCM/methanol (50:1 to 20:1)

Sources & evidence

ORD record
ord-d8ddc8c0662c4591bfd5c562b8754747
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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