Potassium Carbonate → HCID 90403250, compound

HRID 2200671Notes

Reaction equation

HRID 2200671 reaction equation
[CH3:1][N:2]1[C:10]2[N:9]=[C:8]([O:11][CH2:12][CH2:13][O:14][C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([O:21][C:22]([F:25])([F:24])[F:23])[CH:16]=3)[NH:7][C:6]=2[C:5](=[O:26])[N:4]([CH2:27][CH2:28][CH2:29][O:30][CH:31]2[CH2:36][CH2:35][CH2:34][CH2:33][O:32]2)[C:3]1=[O:37].[Cl:38][C:39]1[CH:40]=[CH:41][C:42]([CH2:45]Cl)=[N:43][CH:44]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.CCCC[N+](CCCC)(CCCC)CCCC.[I-]>[Cl:38][C:39]1[CH:40]=[CH:41][C:42]([CH2:45][N:7]2[C:6]3[C:5](=[O:26])[N:4]([CH2:27][CH2:28][CH2:29][O:30][CH:31]4[CH2:36][CH2:35][CH2:34][CH2:33][O:32]4)[C:3](=[O:37])[N:2]([CH3:1])[C:10]=3[N:9]=[C:8]2[O:11][CH2:12][CH2:13][O:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][C:22]([F:23])([F:25])[F:24])[CH:16]=2)=[N:43][CH:44]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 145171515-Chloro-2-(chloromethyl)pyridineHCID 90403316HCID 90403316, compound2×

Product 1

HCID 90403250HCID 90403250, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 3-methyl-1-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)-8-(2-(3-(trifluoromethoxy)phenoxy)ethoxy)-1H-purine-2,6(3H,7H)-dione (60 mg, 0.14 mmol, intermediate 17) in DMF (5 mL) was added 5-chloro-2-(chloromethyl)pyridine (33 mg, 0.20 mmol), potassium carbonate (37 mg, 0.27 mmol) and TBAI (2 mg, 0.02 mmol). The reaction was heated at 50° C. for 8 h. The mixture was cooled and partitioned between ethyl acetate and water. The combined organic layer was dried over sodium sulfate, filtered and concentrated to give crude product, which was used without purification. LCMS MH+-THP 570.

Workup

  1. temperatureThe mixture was cooled
  2. custompartitioned between ethyl acetate and water
  3. dry with materialThe combined organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give crude product, which
  7. customwas used without purification

Sources & evidence

ORD record
ord-c253f1ca527144ac82d67af30b374d8f
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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