Dimethylamine, hydrochloride → HCID 90403041, compound

HRID 2200660Notes

Reaction equation

HRID 2200660 reaction equation
Br[CH2:2][CH2:3][N:4]1[C:12]2[N:11]=[C:10]([O:13][C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([O:20][C:21]([F:24])([F:23])[F:22])[CH:15]=3)[N:9]([CH2:25][C:26]3[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=3)[C:8]=2[C:7](=[O:33])[N:6]([CH3:34])[C:5]1=[O:35].Cl.[CH3:37][NH:38][CH3:39].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C.O>[Cl:32][C:29]1[CH:30]=[CH:31][C:26]([CH2:25][N:9]2[C:8]3[C:7](=[O:33])[N:6]([CH3:34])[C:5](=[O:35])[N:4]([CH2:3][CH2:2][N:38]([CH3:39])[CH3:37])[C:12]=3[N:11]=[C:10]2[O:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][C:21]([F:24])([F:23])[F:22])[CH:15]=2)=[CH:27][CH:28]=1

Participants

7

Reactant 3

HCID 10473Dimethylamine, hydrochlorideHCID 11430Potassium CarbonateHCID 90402845HCID 90402845, compound

Product 1

HCID 90403041HCID 90403041, compoundYield 14.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 3-(2-bromoethyl)-7-(4-chlorobenzyl)-1-methyl-8-(3-(trifluoromethoxy)phenoxy)-1H-purine-2,6(3H,7H)-dione (110 mg, 0.192 mmol) in DMF (3 mL) was added dimethylamine hydrochloride (150 mg, 1.84 mmol), followed by potassium carbonate (100 mg, 0.725 mmol). The mixture was stirred at 40° C. for 16 h; then it was diluted with ethyl acetate and water. The phases were separated and the organic phase was washed with brine, dried over sodium sulfate, filtered and concentrated. The residue was purified by preparative HPLC to give 7-(4-chlorobenzyl)-3-(2-(dimethylamino)ethyl)-1-methyl-8-(3-(trifluoromethoxy)phenoxy)-1H-purine-2,6(3H,7H)-dione (15 mg, 13.3% yield) as white solid.

Workup

  1. customThe phases were separated
  2. washthe organic phase was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-90a348157da04c0ab7f7b1edea283fbe
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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