Potassium Carbonate → HCID 57579073, compound

HRID 881795Notes

Reaction equation

HRID 881795 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[N:14]=[C:13]2[C:9]([N:10]=[CH:11][NH:12]2)=[C:8]([NH2:15])[N:7]=1.[Br:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24]Br)[CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[Br:16][CH2:17][C:18]1[CH:19]=[C:20]([CH:21]=[CH:22][CH:23]=1)[CH2:24][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 69373Benzene, 1,3-bis(bromomethyl)-HCID 178496183HCID 178496183, compound

Product 1

HCID 57579073HCID 57579073, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-(2-Methoxy-ethoxy)-9H-purin-6-ylamine (1 g, 4.78 mmol) (1), α,α′-dibromo-m-xylene (2.52 g, 9.56 mmol) and anhydrous potassium carbonate (1.32 g, 9.56 mmol) were combined in DMF (10 mL) and stirred at ambient temperature for 5 hours. The reaction mixture was diluted with ethyl acetate (120 mL), washed with water (2×), brine, dried with Na2SO4, and evaporated under vacuum. The crude product was purified by chromatography on silica gel with 0-10% methanol in ethyl acetate as eluent. Evaporation of the appropriate fractions gave 9-(3-Bromomethyl-benzyl)-2-(2-methoxy-ethoxy)-9H-purin-6-ylamine (2) (1.1 g, 2.80 mmol, 59%). MS: 392/394 (MH+).

Workup

  1. washwashed with water (2×), brine
  2. dry with materialdried with Na2SO4
  3. customevaporated under vacuum
  4. customThe crude product was purified by chromatography on silica gel with 0-10% methanol in ethyl acetate as eluent
  5. customEvaporation of the appropriate fractions

Sources & evidence

ORD record
ord-13d3717966ca4410b4d5bfb967e10b7e
Source dataset
uspto-grants-2015_03
Patent number
US08993755B2

Reaction notes

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