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

HRID 852043
Notes
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Reaction equation

HRID 852043 reaction equation
[CH3:1][C:2]([CH3:24])([CH3:23])[CH2:3][NH:4][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:30]Br>C(Cl)Cl.O>[Br:30][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[NH:4][CH2:3][C:2]([CH3:24])([CH3:23])[CH3:1]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 24408BromineHCID 516892Sodium BicarbonateHCID 589285373-[6-(2,2-Dimethyl-propylamino)-pyrimidin-4-ylamino]-4,N-dimethyl-benzamide

Product 1

HCID 101359983-{5-Bromo-6-[(2,2-dimethyl-propyl)-amino]-pyrimidin-4-ylamino}-4,n-dimethyl-benzamideYield 56.4%

Reagents, catalysts & solvents 2

HCID 962Water
Solvent
HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-{6-[(2,2-dimethyl-propyl)-amino]-pyrimidin-4-ylamino}-4,N-dimethyl-benzamide (0.45 g, 1.37 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 (314 mg, yield 56%). MS (m/z): 406 (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-58762b739ecc4384a63dc2c975c11829
Source dataset
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07253174B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes