Benzophenone → HCID 58654397, compound

HRID 1170534Notes

Reaction equation

HRID 1170534 reaction equation
Cl.[N:2]1([C:7]2[N:12]=[C:11]([CH2:13][NH2:14])[CH:10]=[C:9]([CH3:15])[N:8]=2)[CH:6]=[CH:5][N:4]=[CH:3]1.C(N(CC)CC)C.[C:23]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)(=O)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>ClCCl>[C:23](=[N:14][CH2:13][C:11]1[CH:10]=[C:9]([CH3:15])[N:8]=[C:7]([N:2]2[CH:6]=[CH:5][N:4]=[CH:3]2)[N:12]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

6

Reactant 4

HCID 3102BenzophenoneHCID 8471TriethylamineHCID 521998p-Toluenesulfonic acid monohydrateHCID 68691971HCID 68691971, compound

Product 1

HCID 58654397HCID 58654397, compoundYield 43.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of (2-(1H-imidazol-1-yl)-6-methylpyrimidin-4-yl)methanamine hydrochloride (20.4 g, 90.3 mmol) and triethylamine (60.0 mL, 452 mmol) in dichloromethane (300 mL) was stirred at room temperature for 30 min then the mixture was concentrated under vacuum. The residue was dissolved in toluene (500 mL) then benzophenone (57.5 g, 316 mmol) and p-toluenesulfonic acid monohydrate (4.50 g, 23.7 mmol) were added to the solution. The mixture was heated to 110° C. for 12 h then concentrated under vacuum. The residue was extracted with ethyl acetate (2×500mL), washed with water (2×100 mL), dried over anhydrous sodium sulfate and concentrated. The product was purified using column chromatography (1:10 EtOAc/hexanes to EtOAc) to afford benzhydrylidene-(2-imidazol-1-yl-6-methyl-pyrimidin-4-ylmethyl)-amine as a yellow solid (14.0 g, 42.6%).

Workup

  1. concentrationthe mixture was concentrated under vacuum
  2. dissolutionThe residue was dissolved in toluene (500 mL)
  3. temperatureThe mixture was heated to 110° C. for 12 h
  4. concentrationthen concentrated under vacuum
  5. extractionThe residue was extracted with ethyl acetate (2×500mL)
  6. washwashed with water (2×100 mL)
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated
  9. customThe product was purified

Sources & evidence

ORD record
ord-6412a6b607d443a49c4a622bdcf193b8
Source dataset
uspto-grants-2010_11
Patent number
US07825256B2

Reaction notes

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