Potassium Carbonate → HCID 90402626, compound

HRID 2200707Notes

Reaction equation

HRID 2200707 reaction equation
[CH3:1][N:2]1[C:10]2[N:9]=[C:8]([CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]([F:22])([F:21])[F:20])[CH:13]=3)[N:7]([CH2:23][C:24]3[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][N:25]=3)[C:6]=2[C:5](=[O:31])[NH:4][C:3]1=[O:32].[OH:33][CH:34]([CH3:48])[CH2:35][CH2:36]OS(C1C=CC(C)=CC=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[OH:33][CH:34]([CH3:48])[CH2:35][CH2:36][N:4]1[C:5](=[O:31])[C:6]2[N:7]([CH2:23][C:24]3[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][N:25]=3)[C:8]([CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]([F:22])([F:21])[F:20])[CH:13]=3)=[N:9][C:10]=2[N:2]([CH3:1])[C:3]1=[O:32]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 132043233-Hydroxybutyl 4-methylbenzenesulfonateHCID 90402690HCID 90402690, compound2×

Product 1

HCID 90402626HCID 90402626, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 3-methyl-7-((5-methylpyridin-2-yl)methyl)-8-(3-(trifluoromethoxy)benzyl)-1H-purine-2,6(3H,7H)-dione (30 mg, 0.067 mmol, intermediate 51) in DMF (3 mL) was added 3-hydroxybutyl-4-methylbenzenesulfonate (24.68 mg, 0.10 mmol), followed by potassium carbonate (27.93 mg, 0.20 mmol). The reaction was stirred at 70° C. for 4 h. The mixture was partitioned between ethyl acetate and water. The organic phase was washed with brine, dried over sodium sulfate, filtered and concentrated to give crude product, which was purified by preparative HPLC to give 1-(3-hydroxybutyl)-3-methyl-7-((5-methylpyridin-2-yl)methyl)-8-(3-(trifluoromethoxy)benzyl)-1H-purine-2,6(3H,7H)-dione (9 mg, 25.8%) as white solid. 1H-NMR (CD3OD) δ 8.216(s,1H), 7.491-7.467(d,1H), 7.312-7.272(m,1H), 7.154-6.995(m,4H), 5.688(s,2H), 4.305(s,2H), 4.143-4.011(m,2H), 3.772-3.440(m,1H), 3.585(s, 3H), 2.283(s,3H), 1.761-1.703(m,2H), 1.194-1.179(d,3H). LCMS retention time 2.569 min; LCMS MH+ 518.

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. washThe organic phase was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give crude product, which
  7. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-4ab2429b57f44f769d9412966fb6c234
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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