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2,4,6-Trimethylaniline → 5-bromo-2-chloro-N-(2,4,6-trimethylphenyl)-4-pyrimidinamine

HRID 41364
Notes
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Reaction equation

HRID 41364 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[NH2:10].[Br:11][C:12]1[C:13]([Cl:19])=[N:14][C:15]([Cl:18])=[N:16][CH:17]=1.CC(N(C(C)C)CC)C>O1CCOCC1>[Br:11][C:12]1[C:13]([Cl:19])=[N:14][C:15]([NH:10][C:3]2[C:4]([CH3:9])=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=2[CH3:1])=[N:16][CH:17]=1.[Br:11][C:12]1[C:13]([NH:10][C:3]2[C:4]([CH3:9])=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=2[CH3:1])=[N:14][C:15]([Cl:18])=[N:16][CH:17]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 69132,4,6-TrimethylanilineHCID 81531DiisopropylethylamineHCID 2899735-Bromo-2,4-dichloropyrimidine

Product 2

HCID 221700865-bromo-2-chloro-N-(2,4,6-trimethylphenyl)-4-pyrimidinamineYield 65%HCID 221701025-bromo4-chloro-N-(2,4,6-trimethylphenyl)-2-pyrimidinamineYield 24%

Reagents, catalysts & solvents

1
HCID 312751,4-DioxaneSolvent2×

Procedure

Reaction under argon atmosphere. A solution of 2,4,6-trimethylbenzenamine (0.00461 mol) in 1,4-dioxane (5 ml) was added to a solution of 5-bromo-2,4-dichloropyrimidine (0.00439 mol) in 1,4-dioxane (5 ml). N,N-bis(1-methylethyl)ethanamine (0.00548 mol) was added. The reaction mixture was stirred and refluxed for 20 hours. The solvent was evaporated. The residue was dissolved in ethyl acetate, washed with a saturated aqueous sodium bicarbonate solution, water and brine, dried with sodium sulfate, filtered, and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: 1:5, 1:2 and 1:1 CH2Cl2:hexane). Two pure fraction groups were collected and their solvent was evaporated, yielding 0.35 g (24%) of 5-bromo-4-chloro-N-(2,4,6-trimethylphenyl)-2-pyrimidinamine (interm. 1) and 0.93 g (65%) of 5-bromo-2-chloro-N-(2,4,6-trimethylphenyl)-4-pyrimidinamine (interim 2).

Workup

  1. customReaction under argon atmosphere
  2. temperaturerefluxed for 20 hours
  3. customThe solvent was evaporated
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with a saturated aqueous sodium bicarbonate solution, water and brine
  6. dry with materialdried with sodium sulfate
  7. filtrationfiltered
  8. customthe solvent was evaporated
  9. customThe residue was purified by column chromatography over silica gel (eluent: 1:5, 1:2 and 1:1 CH2Cl2:hexane)
  10. customTwo pure fraction groups were collected
  11. customtheir solvent was evaporated

Sources & evidence

ORD record
ord-3bb703817bf14abc9d6d994f0b8ceef3
Source dataset
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08530655B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes