Tert-Butyl nitrite → HCID 11278472, compound

HRID 1169885Notes

Reaction equation

HRID 1169885 reaction equation
[CH3:1][C:2]([CH3:19])([CH3:18])[C:3]([O:5][CH2:6][N:7]1[CH:15]=[N:14][C:13]2[C:8]1=[N:9][C:10](N)=[N:11][C:12]=2[Cl:16])=[O:4].[CH3:20][S:21]SC.N(OC(C)(C)C)=O>C(#N)C>[CH3:1][C:2]([CH3:19])([CH3:18])[C:3]([O:5][CH2:6][N:7]1[CH:15]=[N:14][C:13]2[C:8]1=[N:9][C:10]([S:21][CH3:20])=[N:11][C:12]=2[Cl:16])=[O:4]

Participants

5

Reactant 3

HCID 10906Tert-Butyl nitriteHCID 12232Dimethyl DisulfideHCID 11300583HCID 11300583, compound

Product 1

HCID 11278472HCID 11278472, compoundYield 57.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 2-amino-6-chloropurin-9-yl-methyl 2,2-dimethylpropionate 81 (0.566 g, 2 mmol) in acetonitrile (2 mL) was added methyl disulfide (0.94 g, 10 mmol), and tert-butyl nitrite (90%, 1.14 g, 10 mmol) and the resulting reaction mixture was stirred at room temperature for 8 h. The reaction mixture was concentrated in vacuo, and the resulting crude product was subjected to silica gel column chromatography (AcOEt/petroleum ether=1/10), which furnished 82 (0.364 g, 55%): 1H NMR (CDCl3, 300 MHz) δ 8.19 (s, 1H), 6.12 (s, 2H), 2.65 (s, 3H), 1.17 (s, 9H). MS (m/e) (positive-FAB) 315 (M+1)+.

Workup

  1. customthe resulting reaction mixture
  2. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-29d5a5faf4e0462ca80f4c29b03b8be8
Source dataset
uspto-grants-2010_11
Patent number
US07825126B2

Reaction notes

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