Potassium Carbonate → HCID 57816858, compound

HRID 2197459Notes

Reaction equation

HRID 2197459 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[N:14]=[C:13]2[C:9]([NH:10][CH:11]=[N:12]2)=[C:8]([NH2:15])[N:7]=1.[Br:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH2:20]Br.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[Br:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH2:20][N:12]1[CH:11]=[N:10][C:9]2[C:13]1=[N:14][C:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])=[N:7][C:8]=2[NH2:15]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 699793-Bromobenzyl bromideHCID 23079491HCID 23079491, compound

Product 1

HCID 57816858HCID 57816858, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-(2-methoxyethoxy)-9H-purin-6-amine (15) (1.0 g, 4.78 mmol), 3-bromobenzyl bromide (1.5 g, 6.00 mmol) and anhydrous potassium carbonate (0.85 g, 6.15 mmol) were combined in DMF (15 mL) and stirred at room temperature for 16 h. The mixture was diluted with ethyl acetate (150 mL) and washed with water and brine. The organic phase was dried with sodium sulfate and the solvent was removed under vacuum. The resulting residue was triturated with a mixture of diethylether and ethyl acetate (4:1) and filtered. 9-(3-bromobenzyl)-2-(2-methoxyethoxy)-9H-purin-6-amine, Compound (39) (0.77 g, 43%) was obtained as a yellowish solid. 1H-NMR (DMSO) δ: 8.07 (s, 1H), 7.57 (s, 1H), 7.52-7.46 (m, 1H), 7.34-7.22 (m, 4H), 5.26 (s, 2H), 4.32 (t, J=4.5 Hz, 2H), 3.60 (t, J=4.5 Hz, 2H), 3.27 (s, 3H). MS: 378/380 (MH+)

Workup

  1. washwashed with water and brine
  2. dry with materialThe organic phase was dried with sodium sulfate
  3. customthe solvent was removed under vacuum
  4. customThe resulting residue was triturated with a mixture of diethylether and ethyl acetate (4:1)
  5. filtrationfiltered

Sources & evidence

ORD record
ord-1db28bcc6f704e05be6a78d48eafb048
Source dataset
uspto-grants-2012_12
Patent number
US08338593B2

Reaction notes

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