Lithium iodide → (R)-4-(2-chloro-6-(iodomethyl)pyrimidin-4-yl)-3-methylmorpholine
Reaction equation
CS(O[CH2:6][C:7]1[CH:12]=[C:11]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][C@H:14]2[CH3:19])[N:10]=[C:9]([Cl:20])[N:8]=1)(=O)=O.[I-:21].[Li+]>O1CCOCC1>[Cl:20][C:9]1[N:10]=[C:11]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][C@H:14]2[CH3:19])[CH:12]=[C:7]([CH2:6][I:21])[N:8]=1Participants
Conditions
- Temperature
- 107 °C
Procedure
(R)-(2-Chloro-6-(3-methylmorpholino)pyrimidin-4-yl)methyl methanesulfonate (80 g, 248.62 mmol) and lithium iodide (83 g, 621.54 mmol) were dissolved in dioxane (300 ml) and then heated at 107° C. for 1 hour. The reaction mixture was quenched with water (250 ml), extracted with EtOAc (3×250 ml), the organic layer was dried over MgSO4, filtered and evaporated. The residue was dissolved in DCM and Et2O was added, the mixture was passed through silica (4 inches) and eluted with Et2O. Fractions containing product were evaporated and the residue was then triturated with Et2O to give a solid which was collected by filtration and dried under vacuum to afford (R)-4-(2-chloro-6-(iodomethyl)pyrimidin-4-yl)-3-methylmorpholine (75 g, 86%); m/z: (ESI+) MH+, 354.27.
Workup
- customThe reaction mixture was quenched with water (250 ml)
- extractionextracted with EtOAc (3×250 ml)
- dry with materialthe organic layer was dried over MgSO4
- filtrationfiltered
- customevaporated
- dissolutionThe residue was dissolved in DCM
- additionEt2O was added
- washeluted with Et2O
- additionFractions containing product
- customwere evaporated
- customthe residue was then triturated with Et2O
- customto give a solid which
- filtrationwas collected by filtration
- customdried under vacuum
Sources & evidence
- ORD record
- ord-4c1d70b6fd8d49b0940f9e0135f4032a
- Source dataset
- uspto-grants-2012_08
- Patent number
- US08252802B2
Reaction notes
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