Ethyl bromoacetate → (2-Amino-6-iodopurin-9-yl)-acetic acid ethyl ester

HRID 857544Notes

Reaction equation

HRID 857544 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4]([I:11])[N:3]=1.Br[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:17]([O:16][C:14](=[O:15])[CH2:13][N:8]1[CH:7]=[N:6][C:5]2[C:9]1=[N:10][C:2]([NH2:1])=[N:3][C:4]=2[I:11])[CH3:18]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 61015752-Amino-6-iodopurine

Product 1

HCID 85849531(2-Amino-6-iodopurin-9-yl)-acetic acid ethyl esterYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-amino-6-iodo-purine (78.3 g, 0.3 mol) in DMF (1960 mL) was added ethyl bromoacetate (55.1 g, 0.33 mol) and potassium carbonate (82.9 g, 0.6 mol). The resulting reaction mixture was stirred for 12 h at room temperature. The reaction mixture was concentrated to small volume (about 150 mL) in vacuo and the residue was dissolved in water. The solid was filtered off, washed with water and ethyl ether, and dried in vacuo to give the titled compound (98.4 g, 95%). 1H-NMR (50 MHz; DMSO-d6) δ 8.06 (s, 1H), 6.90 (br.s, 2H), 4.94 (s, 2H), 4.17 (q, 2H), 1.22 (t, 3H).

Workup

  1. customThe resulting reaction mixture
  2. concentrationThe reaction mixture was concentrated to small volume (about 150 mL) in vacuo
  3. dissolutionthe residue was dissolved in water
  4. filtrationThe solid was filtered off
  5. washwashed with water and ethyl ether
  6. customdried in vacuo

Sources & evidence

ORD record
ord-927e117cf3aa4818a94eba31ec9295bb
Source dataset
uspto-grants-2006_12
Patent number
US07145006B2

Reaction notes

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