Sodium periodate → (R)-4-(2-chloro-6-(methylsulfinylmethyl)pyrimidin-4-yl)-3-methylmorpholine

HRID 888988Notes

Reaction equation

I([O-])(=O)(=O)=[O:2].[Na+].[Cl:7][C:8]1[N:13]=[C:12]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][C@H:15]2[CH3:20])[CH:11]=[C:10]([CH2:21][S:22][CH3:23])[N:9]=1>O.CCOC(C)=O.CO.C(Cl)Cl>[Cl:7][C:8]1[N:13]=[C:12]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][C@H:15]2[CH3:20])[CH:11]=[C:10]([CH2:21][S:22]([CH3:23])=[O:2])[N:9]=1

Participants

Conditions

Temperature: 20 °C

Procedure

Sodium meta-periodate (2.87 g, 13.44 mmol) was added in one portion to (R)-4-(2-chloro-6-(methylthiomethyl)pyrimidin-4-yl)-3-methylmorpholine (3.68 g, 13.44 mmol) in water (10.00 ml), EtOAc (20 ml) and MeOH (10.00 ml). The resulting solution was stirred at 20° C. for 16 hours. The reaction mixture was diluted with DCM (60 ml) and then filtered. The DCM layer was separated and the aqueous layer washed with DCM (3×40 ml). The organics were combined, dried over MgSO4, filtered and then evaporated. The residue was purified by flash chromatography on silica, eluting with a gradient of 0 to 7% MeOH in DCM. Pure fractions were evaporated to afford (R)-4-(2-chloro-6-(methylsulfinylmethyl)pyrimidin-4-yl)-3-methylmorpholine (2.72 g, 70%); 1H NMR (400 MHz, DMSO-d6) 1.22 (3H, d), 2.64 (3H, d), 3.14-3.26 (1H, m), 3.45 (1H, td), 3.59 (1H, dd), 3.73 (1H, d), 3.88-3.96 (2H, m), 4.00 (1H, d), 4.07 (1H, dt), 4.33 (1H, s), 6.81 (1H, s); m/z: (ESI+) MH30, 290.43.

Workup

filtrationfiltered
customThe DCM layer was separated
washthe aqueous layer washed with DCM (3×40 ml)
dry with materialdried over MgSO4
filtrationfiltered
customevaporated
customThe residue was purified by flash chromatography on silica
washeluting with a gradient of 0 to 7% MeOH in DCM
customPure fractions were evaporated

Sources & evidence

ORD record: ord-a8db6b9fcbab4c8d9c18df77b0e9fd5d
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08252802B2

Reaction notes

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