3-{5-Cyano-6-[(2,2-dimethyl-propyl)-methyl-amino]-2-methylsulfanyl-pyrimidin-4-ylamino}-N-methoxy-4-methyl-benzamide → 3-{5-Cyano-6-[(2,2-dimethyl-propyl)-methyl-amino]-2-methanesulfinyl-pyrimidin-4-ylamino}-N-methoxy-4-methyl-benzamide

HRID 1666075Notes

Reaction equation

[C:1]([C:3]1[C:4]([NH:18][C:19]2[CH:20]=[C:21]([CH:27]=[CH:28][C:29]=2[CH3:30])[C:22]([NH:24][O:25][CH3:26])=[O:23])=[N:5][C:6]([S:16][CH3:17])=[N:7][C:8]=1[N:9]([CH2:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH3:10])#[N:2].I([O-])(=O)(=O)=[O:32].[Na+]>C(O)C.O>[C:1]([C:3]1[C:4]([NH:18][C:19]2[CH:20]=[C:21]([CH:27]=[CH:28][C:29]=2[CH3:30])[C:22]([NH:24][O:25][CH3:26])=[O:23])=[N:5][C:6]([S:16]([CH3:17])=[O:32])=[N:7][C:8]=1[N:9]([CH2:11][C:12]([CH3:13])([CH3:14])[CH3:15])[CH3:10])#[N:2]

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 3-{5-Cyano-6-[(2,2-dimethyl-propyl)-methyl-amino]-2-methylsulfanyl-pyrimidin-4-ylamino}-N-methoxy-4-methyl-benzamide (0.10 g) in ethanol (5 mL) was added the solution of sodium periodate (0.2 g) in water (1 mL). The resulting solution was heated to 70° C. for overnight. The solvent was evaporated and the residue was partitioned between water and ethyl acetate. The organic layer was separated, and concentrated, and the residue was purified by silica gel column chromatography to afford the sulfoxide product (90 mg). MS (m/z): 445 (M+H).

Workup

customThe solvent was evaporated
customthe residue was partitioned between water and ethyl acetate
customThe organic layer was separated
concentrationconcentrated
customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-02fbd6d834114fe6ac4c853b42c28df7
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08044040B2

Reaction notes

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