Aniline → 2-anilino-6-(2-chlorophenyl)imidazo[1,2-a]pyrimido[5,4-e]pyrimidin-5(6H)-one

HRID 2370614Notes

Reaction equation

HRID 2370614 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][CH:29]=[CH:28][CH:27]=1.C([O-])(O)=O.[Na+].[Cl-].[Na+].O>>[NH:25]([C:13]1[N:14]=[CH:15][C:16]2[C:17](=[O:18])[N:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])[C:9]3[N:10]([CH:22]=[CH:23][N:24]=3)[C:11]=2[N:12]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

4

Reactant 3

HCID 6115AnilineHCID 681947574-(2-Chloro-phenyl)-8-methanesulfinyl-4H-3,4,7,9,9b-pentaaza-cyclopenta[a]naphthalen-5-oneHCID 129703874Sodium hydrogencarbonate brine

Product 1

HCID 601684962-anilino-6-(2-chlorophenyl)imidazo[1,2-a]pyrimido[5,4-e]pyrimidin-5(6H)-one

Procedure

A mixture of Example 1E (70.0 mg, 0.195 mmol) and aniline (39.1 μl, 0.428 mmol) was heated in a capped vial at 90° C. for 1 hour. After cooling, the residue was treated with saturated NaHCO3/brine and extracted with ethyl acetate (2×). 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, DMSO-d6) δ ppm 7.08 (d, J=1.83 Hz, 1H), 7.14 (t, J=7.48 Hz, 1H), 7.42 (t, J=7.63 Hz, 2H), 7.54-7.59 (m, 2H), 7.61-7.66 (m, 1H), 7.70-7.74 (m, 1H), 7.79-7.90 (m, 3H), 9.14 (s, 1H), 10.78 (s, 1H). MS (ESI+) m/z 389.2 (M+H)+.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate (2×)
  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-bb9c52b499604d0289f1e07428d509ef
Source dataset
uspto-grants-2014_04
Patent number
US08710065B2

Reaction notes

Loading…