Methyl iodide → HCID 59605850, compound

HRID 1945695Notes

Reaction equation

HRID 1945695 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][NH:8]2)=[C:4]([N:11]2[CH:16]3[CH2:17][CH2:18][CH:12]2[CH2:13][O:14][CH2:15]3)[N:3]=1.CI.[C:21]([O-])([O-])=O.[K+].[K+]>C1COCC1>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH3:21])=[C:4]([N:11]2[CH:12]3[CH2:18][CH2:17][CH:16]2[CH2:15][O:14][CH2:13]3)[N:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodide2×HCID 11430Potassium CarbonateHCID 178478368HCID 178478368, compound

Product 1

HCID 59605850HCID 59605850, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-chloro-6-(3-oxa-8-azabicyclo[3.2.1]oct-8-yl)-9H-purine (650 mg, 2.45 mmol), methyl iodide (183 μL, 2.94 mmol) and K2CO3 (473 mg, 3.43 mmol) in THF (15 mL) was stirred at r.t. for 18 h before further methyl iodide (50 μL, 0.80 mmol) was added. The resulting mixture was allowed to stir for 65 h then concentrated in vacuo. The resulting residue was partitioned between EtOAc and H2O, the organic phase washed with brine, then dried (Na2SO4) and concentrated in vacuo affording the title compound as an off-white solid (673 mg, 98%). LCMS (method H): RT 2.63 min [M+H]+ 280.3

Workup

  1. additionwas added
  2. concentrationthen concentrated in vacuo
  3. customThe resulting residue was partitioned between EtOAc and H2O
  4. washthe organic phase washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f5385dd713e94b41821eb5ec86ddc967
Source dataset
uspto-grants-2013_03
Patent number
US08394796B2

Reaction notes

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