Potassium Carbonate → HCID 90402769, compound

HRID 2200661Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 8-bromo-7-(4-chlorobenzyl)-3-methyl-1-(2-(2-(tetrahydro-2H-pyran-2-yloxy)ethoxy)ethyl)-1H-purine-2,6(3H,7H)-dione (150 mg, 0.28 mmol, intermediate 11) in DMF (5 mL) was added 4-chloro-3-(trifluoromethyl)phenol (81 mg, 0.45 mmol) and potassium carbonate (76 mg, 0.55 mmol). The mixture was stirred at 80° C. overnight. 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 a crude product which was used without purification. LCMS retention time 2.112 min; LCMS MH+-THP 573.

Workup

customThe mixture was partitioned between ethyl acetate and water
washThe organic phase was washed with brine
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-02a1c2609d824bb4957080a8799a8a80
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09359359B2

Reaction notes

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