Dimethylamine → HCID 90403241, compound

HRID 2200644Notes

Reaction equation

HRID 2200644 reaction equation
Br[CH2:2][CH2:3][N:4]1[C:12](=[O:13])[C:11]2[N:10]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=3)[C:9]([O:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([O:29][C:30]([F:33])([F:32])[F:31])[CH:24]=3)=[N:8][C:7]=2[N:6]([CH3:34])[C:5]1=[O:35].[CH3:36][NH:37][CH3:38]>C(OCC)(=O)C.O>[ClH:21].[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([CH2:14][N:10]2[C:11]3[C:12](=[O:13])[N:4]([CH2:3][CH2:2][N:37]([CH3:38])[CH3:36])[C:5](=[O:35])[N:6]([CH3:34])[C:7]=3[N:8]=[C:9]2[O:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([O:29][C:30]([F:33])([F:32])[F:31])[CH:24]=2)=[CH:16][CH:17]=1

Participants

5

Reactant 2

HCID 674DimethylamineHCID 90403212HCID 90403212, compound

Product 1

HCID 90403241HCID 90403241, compoundYield 25.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

1-(2-bromoethyl)-7-(4-chlorobenzyl)-3-methyl-8-(3-(trifluoromethoxy)phenoxy)-1H-purine-2,6(3H,7H)-dione (120 mg, 0.0.210 mmol) was dissolved in aqueous dimethylamine (3 mL), then the mixture was heated to 100° C. in a sealed tube with stirring overnight. The mixture was diluted with ethyl acetate and water, and the phases were separated. The organic phase was washed with brine, dried over sodium sulfate, filtered and concentrated to give crude product, which was purified by preparative HPLC and lyophilized to give 7-(4-chlorobenzyl)-1-(2-(dimethylamino)ethyl)-3-methyl-8-(3-(trifluoromethoxy)phenoxy)-1H-purine-2,6(3H,7H)-dione hydrochloride (29 mg, 25.6% yield) as white solid. 1H-NMR (DMSO-d6) δ 9.67(s, 1H), 7.64-7.60(t, 1H), 7.47-7.41(m, 6H), 7.36-7.34(m, 1H), 5.46(s, 2H), 4.23-4.21(m, 2H), 3.37-3.34(m, 2H), 3.31(s, 3H), 2.87-2.86(d, 6H). LCMS retention time 2.174 min; LCMS MH+ 538.

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. customto give crude product, which
  7. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-33b8c95fd0754901a86d4e4a09a93755
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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