p-Toluidine → 6-(2-chlorophenyl)-2-[(4-methylphenyl)amino]imidazo[1,2-a]pyrimido[5,4-e]pyrimidin-5(6H)-one

HRID 2370626Notes

Reaction equation

HRID 2370626 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:17](=[O:18])[C:16]2[C:11](=[N:12][C:13](S(C)=O)=[N:14][CH:15]=2)[N:10]2[CH:22]=[CH:23][N:24]=[C:9]12.[NH2:25][C:26]1[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=1.C([O-])(O)=O.[Na+]>[Cl-].[Na+].O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:17](=[O:18])[C:16]2[CH:15]=[N:14][C:13]([NH:25][C:26]3[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=3)=[N:12][C:11]=2[N:10]2[CH:22]=[CH:23][N:24]=[C:9]12

Participants

5

Reactant 3

HCID 7813p-ToluidineHCID 516892Sodium BicarbonateHCID 681947574-(2-Chloro-phenyl)-8-methanesulfinyl-4H-3,4,7,9,9b-pentaaza-cyclopenta[a]naphthalen-5-one

Product 1

HCID 681946046-(2-chlorophenyl)-2-[(4-methylphenyl)amino]imidazo[1,2-a]pyrimido[5,4-e]pyrimidin-5(6H)-one

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of Example 1E (132.0 mg, 0.367 mmol) and p-toluidine (86 mg, 0.807 mmol) was heated in a capped vial at 90° C. for 1 hour. After cooling, the residue was treated with saturated aqueous NaHCO3 and brine and extracted with ethyl acetate (twice). The combined organic layers were dried over MgSO4, filtered, concentrated, and purified on a 12 g column using the ISCO Companion flash system eluting with CH2Cl2/ethyl acetate (8:2 to 7:3) to provide the title compound. 1H NMR (400 MHz, CDCl3) δ 2.39 (s, 3H), 7.08 (d, J=1.8 Hz, 1H), 7.26-7.23 (m, 2H), 7.49-7.47 (m, 3H), 7.57-7.55 (m, 2H), 7.66-7.61 (m, 1H), 7.72-7.67 (m, 1H), 7.88-7.72 (m, 1H), 9.24 (s, 1H). MS (ESI+) m/z 403.2 (M+H)+.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate (twice)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified on a 12 g column
  7. washeluting with CH2Cl2/ethyl acetate (8:2 to 7:3)

Sources & evidence

ORD record
ord-51e0db15355c47158ee9fd31b7552d3a
Source dataset
uspto-grants-2014_04
Patent number
US08710065B2

Reaction notes

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