Sulfuric acid magnesium salt (1:1) → HCID 10162037, compound

HRID 1666080Notes

Reaction equation

HRID 1666080 reaction equation
[CH3:1][C:2]([CH3:27])([CH3:26])[CH2:3][N:4]([CH3:25])[C:5]1[N:10]=[C:9]([S:11][CH3:12])[N:8]=[C:7]([NH:13][C:14]2[CH:15]=[C:16]([CH:21]=[CH:22][C:23]=2[CH3:24])[C:17]([NH:19][CH3:20])=[O:18])[CH:6]=1.C(=O)(O)[O-].[Na+].[Br:33]Br.S([O-])([O-])(=O)=O.[Mg+2]>C(Cl)Cl.C(OCC)(=O)C>[Br:33][C:6]1[C:7]([NH:13][C:14]2[CH:15]=[C:16]([CH:21]=[CH:22][C:23]=2[CH3:24])[C:17]([NH:19][CH3:20])=[O:18])=[N:8][C:9]([S:11][CH3:12])=[N:10][C:5]=1[N:4]([CH2:3][C:2]([CH3:27])([CH3:26])[CH3:1])[CH3:25]

Participants

7

Reactant 4

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 24408BromineHCID 516892Sodium BicarbonateHCID 58928553HCID 58928553, compound

Product 1

HCID 10162037HCID 10162037, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-{6-[(2,2-dimethyl-propyl)-methyl-amino]-2-methylsulfanyl-pyrimidin-4-ylamino}-4,N-dimethyl-benzamide (0.10 g) in methylene chloride (2 mL), was added sat. aq. sodium bicarbonate (0.05 mL) and bromine (0.013 mL). The resulting mixture was stirred at room temperature for 30 minutes, and ethyl acetate (30 mL) and magnesium sulfate (1 g) was added. After filtration and concentration, the residue was purified by silica gel column chromatography to afford the product (61.9 mg). MS (m/z): 466 (M+H).

Workup

  1. filtrationAfter filtration and concentration
  2. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c624bceff5994301afe99eee5adc77fc
Source dataset
uspto-grants-2011_10
Patent number
US08044040B2

Reaction notes

Loading…