Ethyl bromoacetate → Ethyl 2,6-dichloro-9H-purine-9-acetate

HRID 271268Notes

Reaction equation

HRID 271268 reaction equation
[Cl:1][C:2]1[NH:3][C:4]([Cl:11])=[C:5]2[C:9]([N:10]=1)=[N:8][CH:7]=[N:6]2.[H-].[Na+].Br[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17].C([O-])(O)=O.[Na+]>C1COCC1>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:4]([Cl:11])[N:3]=1

Participants

6

Reactant 4

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 178478323HCID 178478323, compound

Product 1

HCID 58102459Ethyl 2,6-dichloro-9H-purine-9-acetateYield 53.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

An ice-cold solution of 2,6-dichloro-1H-purine (1.89 g, 10 mmol) in THF (10 mL) was treated with NaH (60% in oil, 440 mg, 11 mmol), stirred at 0° C. for 30 min, treated with ethyl bromoacetate (1.22 mL, 11 mmol), stirred at room temperature for 2 h, poured into sat. NaHCO3, extracted with EtOAc and the combined organic phase dried (MgSO4), concentrated in vacuo and purified by chromatography [SiO2; Heptane:EtOAc (2:1)] to give the title compound (1.46 g, 53%) as a white solid: IR νmax (Nujol)/cm−1 3106, 2985, 2955, 2924, 2854, 1734, 1598, 1557, 1374, 1341, 1298, 1156 and 884; NMR δH (400 MHz, CDCl3) 1.31 (3H, t, J7.0 Hz), 4.29 (2H, q, J7.0 Hz), 5.01 (2H, s), 8.17 (1H, s).

Workup

  1. stirringstirred at room temperature for 2 h
  2. extractionextracted with EtOAc
  3. dry with materialthe combined organic phase dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. custompurified by chromatography [SiO2; Heptane:EtOAc (2:1)]

Sources & evidence

ORD record
ord-153185ed6827460b89ff207d8cb42b09
Source dataset
uspto-grants-2008_11
Patent number
US07452894B2

Reaction notes

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