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

HRID 1294431

반응식

HRID 1294431 반응식
[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

참가 물질

6

반응물 3

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

생성물 2

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

시약·촉매·용매 1

HCID 312751,4-Dioxane용매2회

실험 절차

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 (intern. 1) and 0.93 g (65%) of 5-bromo-2-chloro-N-(2,4,6-trimethylphenyl)-4-pyrimidinamine (interm. 2).

후처리

  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

출처 및 근거

ORD 기록
ord-507fc978a6c14121915e6a556752bda5
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07241458B1

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