Sodium Hydroxide → 6-Chloro-2-(methylsulfanyl)-7H-purine

HRID 1169886Notes

Reaction equation

HRID 1169886 reaction equation
CC(C)(C)C(OC[N:7]1[CH:15]=[N:14][C:13]2[C:8]1=[N:9][C:10]([S:17][CH3:18])=[N:11][C:12]=2[Cl:16])=O.[OH-].[Na+]>CC(O)C.C1COCC1>[Cl:16][C:12]1[N:11]=[C:10]([S:17][CH3:18])[N:9]=[C:8]2[C:13]=1[NH:14][CH:15]=[N:7]2

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 11278472HCID 11278472, compound

Product 1

HCID 112641216-Chloro-2-(methylsulfanyl)-7H-purineYield 56%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-chloro-2-methylthiopurin-9-ylmethyl 2,2-dimethylpropionate (82) (0.314 g, 1 mmol) in i-PrOH (10 mL) and THF (25 mL) was added 2N aq NaOH (2 mL) and the resulting reaction mixture was stirred at room temperature for 12 hr. The reaction mixture was concentrated under reduced pressure and the residue obtained was purified by silica gel column chromatography (AcOEt/petroleum ether=3/7) which afforded 83 (0.112 g, 56%): 1H NMR (DMSO-d6, 300 MHz) δ 8.54 (s, 1H), 2.58 (s, 3H) MS (m/e) (positive-FAB) 200.9 (M+1)+.

Workup

  1. customthe resulting reaction mixture
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue obtained
  4. customwas purified by silica gel column chromatography (AcOEt/petroleum ether=3/7) which

Sources & evidence

ORD record
ord-12f77971f25049098c873154ba704c52
Source dataset
uspto-grants-2010_11
Patent number
US07825126B2

Reaction notes

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