Ethanol → HCID 59239340, compound

HRID 1698037Notes

Reaction equation

HRID 1698037 reaction equation
[NH2:1][CH:2]([CH3:36])[CH2:3][NH:4][C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:15]=[C:16]([N:30]3[CH2:35][CH2:34][O:33][CH2:32][CH2:31]3)[C:17]3[CH2:23][CH2:22][N:21]([C:24]4[N:29]=[CH:28][CH:27]=[CH:26][N:25]=4)[CH2:20][C:18]=3[N:19]=2)=[CH:10][CH:9]=1)=S.C(O)C>[Hg]=O>[CH3:36][CH:2]1[NH:1][C:5]([NH:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]3[N:15]=[C:16]([N:30]4[CH2:31][CH2:32][O:33][CH2:34][CH2:35]4)[C:17]4[CH2:23][CH2:22][N:21]([C:24]5[N:29]=[CH:28][CH:27]=[CH:26][N:25]=5)[CH2:20][C:18]=4[N:19]=3)=[CH:10][CH:9]=2)=[N:4][CH2:3]1

Participants

4

Reactant 2

HCID 702EthanolHCID 86640114HCID 86640114, compound

Product 1

HCID 59239340HCID 59239340, compound

Reagents, catalysts & solvents 1

HCID 30856Mercuric oxideCatalyst

Procedure

Step 2—Synthesis of compound xk: 1-(2-aminopropyl)-3-(4-(4-morpholino-7-(pyrimidin-2-yl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)thiourea (0.293 g, 0.000579 mol) in dry Ethanol (12.0 mL, 0.206 mol) was added Mercury(II) oxide (0.260 g, 0.00120 mol). The reaction mixture was stirred at room temperature for 8 hours. The reaction mixture was heated at 40° C. and stirred overnight. The reaction mixture was heated at 50° C. and stirred overnight. The reaction mixture was heated at 78° C. for 8 hours. The reaction mixture was cooled to room temperature and stirred for 6 days. The reaction mixture was heated at 78° C. for 8 hours. The reaction mixture was cooled to room temperature, filtered through celite, filtered through a disc filter, concentrated, and purified by HPLC. 1H NMR (400 MHz, DMSO) δ 8.43 (d, J=4.7, 2H), 8.17 (d, J=8.5, 2H), 7.01 (s, 2H), 6.69 (t, J=4.7, 1H), 6.32 (s, 2H), 4.80 (s, 2H), 3.98 (s, 2H), 3.82-3.70 (m, 5H), 3.46 (s, 5H), 2.92 (s, 1H), 2.75 (s, 2H), 1.15 (d, J=6.1, 3H). LC/MS-m/z+472.2 (M+H)+

Workup

  1. temperatureThe reaction mixture was heated at 40° C.
  2. stirringstirred overnight
  3. temperatureThe reaction mixture was heated at 50° C.
  4. stirringstirred overnight
  5. temperatureThe reaction mixture was heated at 78° C. for 8 hours
  6. temperatureThe reaction mixture was cooled to room temperature
  7. stirringstirred for 6 days
  8. temperatureThe reaction mixture was heated at 78° C. for 8 hours
  9. temperatureThe reaction mixture was cooled to room temperature
  10. filtrationfiltered through celite
  11. filtrationfiltered through a disc
  12. filtrationfilter
  13. concentrationconcentrated
  14. custompurified by HPLC

Sources & evidence

ORD record
ord-aa773dae312641c8b155966a57d836de
Source dataset
uspto-grants-2012_04
Patent number
US08163763B2

Reaction notes

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