Sodium Hydroxide → 4,6-Diamino-5-(1,2-bis(4-isopropylphenyl)ethenyl)pyrimidine

HRID 378246

반응식

HRID 378246 반응식
[CH3:1][CH:2]([C:4]1[CH:9]=[CH:8][C:7]([C:10]#[C:11][C:12]2[CH:17]=[CH:16][C:15]([CH:18]([CH3:20])[CH3:19])=[CH:14][CH:13]=2)=[CH:6][CH:5]=1)[CH3:3].[B]1OC2C(=CC=CC=2)O1.[NH2:30][C:31]1[C:36](I)=[C:35]([NH2:38])[N:34]=[CH:33][N:32]=1.C(=O)(O)[O-].[Na+].[OH-].[Na+]>C1COCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:30][C:31]1[C:36]([C:10]([C:7]2[CH:8]=[CH:9][C:4]([CH:2]([CH3:1])[CH3:3])=[CH:5][CH:6]=2)=[CH:11][C:12]2[CH:13]=[CH:14][C:15]([CH:18]([CH3:20])[CH3:19])=[CH:16][CH:17]=2)=[C:35]([NH2:38])[N:34]=[CH:33][N:32]=1

참가 물질

9

반응물 5

HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 6327445BenzcatechinboraneHCID 112540441,2-Bis(4-(2-propyl)phenyl)acetyleneHCID 113109004,6-Pyrimidinediamine, 5-iodo-

생성물 1

HCID 536772854,6-Diamino-5-(1,2-bis(4-isopropylphenyl)ethenyl)pyrimidine수율 28%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

실험 절차

1,2-Bis(4-(2-propyl)phenyl)acetylene (11.40 g, 43 mmol) was dissolved in 50 mL THF, catecholborane (1 M, 50 mL) in THF was added, and the mixture was heated at reflux for 30 hours. The mixture was cooled, then 4,6-diamino-5-iodo-pyrimidine, 30 mL saturated aqueous sodium bicarbonate, 20 mL 3N aqueous sodium hydroxide, and 1.00 g (0.87 mmol) tetrakis(triphenylphosphine)palladium(0) were added. The mixture was heated to reflux for 18 hours, cooled, diluted with water, then extracted with ethyl acetate. The organic layers were combined, dried with magnesium sulfate, and the solvent evaporated. The residue was chromatographed on silica gel with 2.5% to 5% (19:1 ethanol:ammonium hydroxide) in ethyl acetate to give the desired product (4.53 g, 28% yield).

후처리

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 30 hours
  3. temperatureThe mixture was cooled
  4. temperatureThe mixture was heated
  5. temperatureto reflux for 18 hours
  6. temperaturecooled
  7. extractionextracted with ethyl acetate
  8. dry with materialdried with magnesium sulfate
  9. customthe solvent evaporated
  10. customThe residue was chromatographed on silica gel with 2.5% to 5% (19:1 ethanol:ammonium hydroxide) in ethyl acetate

출처 및 근거

ORD 기록
ord-758c379a3dcf468f97ba429b58b3c21e
출처 데이터셋
uspto-grants-2000_02
특허 번호
US06030969

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