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

HRID 378246

Reaction equation

HRID 378246 reaction equation
[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

Participants

9

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-758c379a3dcf468f97ba429b58b3c21e
Source dataset
uspto-grants-2000_02
Patent number
US06030969

Linked notes

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