Bromine → 3-{5-Bromo-6-[(2,2-dimethyl-propyl)-methyl-amino]-pyrimidin-4-ylamino}-4,n-dimethyl-benzamide

HRID 1666088Notes

Reaction equation

HRID 1666088 reaction equation
[CH3:1][C:2]([CH3:25])([CH3:24])[CH2:3][N:4]([CH3:23])[C:5]1[N:10]=[CH:9][N:8]=[C:7]([NH:11][C:12]2[CH:13]=[C:14]([CH:19]=[CH:20][C:21]=2[CH3:22])[C:15]([NH:17][CH3:18])=[O:16])[CH:6]=1.C(=O)(O)[O-].[Na+].[Br:31]Br>C(Cl)Cl.O>[Br:31][C:6]1[C:7]([NH:11][C:12]2[CH:13]=[C:14]([CH:19]=[CH:20][C:21]=2[CH3:22])[C:15]([NH:17][CH3:18])=[O:16])=[N:8][CH:9]=[N:10][C:5]=1[N:4]([CH2:3][C:2]([CH3:25])([CH3:24])[CH3:1])[CH3:23]

Participants

6

Reactant 3

HCID 24408BromineHCID 516892Sodium BicarbonateHCID 589285053-{6-[(2,2-Dimethyl-propyl)-methyl-amino]-pyrimidin-4-ylamino}-4,N-dimethyl-benzamide

Product 1

HCID 589285453-{5-Bromo-6-[(2,2-dimethyl-propyl)-methyl-amino]-pyrimidin-4-ylamino}-4,n-dimethyl-benzamideYield 44.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-{6-[(2,2-dimethyl-propyl)-methyl-amino]-pyrimidin-4-ylamino}-4,N-dimethyl-benzamide (0.46 g, 1.34 mmol) in methylene chloride (10 mL), was added sat. aq. sodium bicarbonate (2 mL) and bromine (0.07 mL, 1.37 mmol). The resulting mixture was stirred at room temperature for 18 hours, and the reaction was then diluted with water (20 mL). The organic layer was separated and the aqueous layer was extracted with DCM (10 mL). The combined organic layer was dried (sodium sulfate), filtered and concentrated. The residue was purified by silica gel column chromatography using 2% methanol in DCM as eluent to afford the product (250 mg, yield 44%). MS (m/z): 420 (M+H).

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with DCM (10 mL)
  3. dry with materialThe combined organic layer was dried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-08a4ebad2ab34b59a361cce53c5b126e
Source dataset
uspto-grants-2011_10
Patent number
US08044040B2

Reaction notes

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