Potassium Carbonate → HCID 59649128, compound

HRID 2197470Notes

Reaction equation

HRID 2197470 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4]([NH2:11])[N:3]=1.[Br:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH2:16]Br.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[Br:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH2:16][N:8]1[CH:7]=[N:6][C:5]2[C:9]1=[N:10][C:2]([Cl:1])=[N:3][C:4]=2[NH2:11]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 699793-Bromobenzyl bromideHCID 949042-Chloroadenine

Product 1

HCID 59649128HCID 59649128, compoundYield 75.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Chloroadenine (1.53 g, 9.0 mmol), 3-bromobenzyl bromide (2.48 g, 9.92 mmol), potassium carbonate (1.38 g, 10 mmol) were combined in DMF (10 mL) and stirred at ambient temperature overnight. The mixture was diluted with ethyl acetate (200 mL) and washed with water and brine. The organic layer was dried with Na2SO4 and evaporated to dryness. The residue was triturated with diethyl ether/ethyl acetate 4:1 and filtered giving 9-(3-bromobenzyl)-2-chloro-9H-purin-6-amine (Compound 53) (2.3 g) as off-white solid.

Workup

  1. washwashed with water and brine
  2. dry with materialThe organic layer was dried with Na2SO4
  3. customevaporated to dryness
  4. customThe residue was triturated with diethyl ether/ethyl acetate 4:1
  5. filtrationfiltered

Sources & evidence

ORD record
ord-93f4ce8ce4c14e548180474bc12f46c5
Source dataset
uspto-grants-2012_12
Patent number
US08338593B2

Reaction notes

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