Methyl iodide → (S)-4-(2-chloro-9-methyl-9H-purin-6-yl)-3-methylmorpholine

HRID 1945699Notes

Reaction equation

HRID 1945699 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[CH2:16][CH2:15][O:14][CH2:13][C@@H:12]2[CH3:17])[N:3]=1.CI.[C:20]([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[CH3:20])=[C:4]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][C@@H:12]2[CH3:17])[N:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178461593HCID 178461593, compound

Product 1

HCID 58222544(S)-4-(2-chloro-9-methyl-9H-purin-6-yl)-3-methylmorpholineYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-chloro-6-((S)-3-methylmorpholin-4-yl)-9H-purine (5.3 g, 20.89 mmol), methyl iodide (1.6 mL, 25.70 mmol) and K2CO3 (4.0 g, 28.94 mmol) in THF (100 mL) were stirred at r.t. for 18 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 (4.84 g, 87%). LCMS (method H): RT 2.74 min [M+H]+ 268.2

Workup

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

Sources & evidence

ORD record
ord-29905b4932b44a5d90f5f866dbb299eb
Source dataset
uspto-grants-2013_03
Patent number
US08394796B2

Reaction notes

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