Potassium Carbonate → HCID 54484017, compound

HRID 2291849Notes

Reaction equation

HRID 2291849 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4]([Cl:11])[N:3]=1.[CH2:12]([O:14][C:15](=[O:22])[CH:16]([CH2:20][OH:21])[CH2:17][CH2:18]Br)[CH3:13].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:12]([O:14][C:15](=[O:22])[CH:16]([CH2:20][OH:21])[CH2:17][CH2:18][N:8]1[CH:7]=[N:6][C:5]2[C:9]1=[N:10][C:2]([NH2:1])=[N:3][C:4]=2[Cl:11])[CH3:13]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 53603492-Amino-6-chloropurineHCID 54388651HCID 54388651, compound

Product 1

HCID 54484017HCID 54484017, compoundYield 15.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Amino-6-chloropurine (3.37 g, 19.9 mmol), 4-bromo-2-hydroxymethylbutyric acid ethyl ester (4.49 g, 19.9 mmol) and anhydrous potassium carbonate (2.75 g, 19.9 mmol) were mixed with 50 ml of dimethylformamide and the mixture was stirred at room temperature during 92 hours. The mixture was then filtered and the filtrate evaporated. The residue was extracted with 3×50 ml chloroform and the combined extracts were evaporated. Flash chromatography (silica gel, chloroform-methanol 10:1) and two recrystallizations from water afforded 0.995 g of the 4-(2-amino-6-chloropurin-9-yl)-2-hydroxymethylbutyric acid ethyl ester.

Workup

  1. filtrationThe mixture was then filtered
  2. customthe filtrate evaporated
  3. extractionThe residue was extracted with 3×50 ml chloroform
  4. customthe combined extracts were evaporated
  5. customFlash chromatography (silica gel, chloroform-methanol 10:1) and two recrystallizations from water

Sources & evidence

ORD record
ord-f805bb5216b24b80b8329b24fed0470d
Source dataset
uspto-grants-1989_01
Patent number
US04798833

Reaction notes

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