Potassium Hydroxide → HCID 178518662, compound

HRID 600460Notes

Reaction equation

HRID 600460 reaction equation
[OH-:1].[K+].Cl[C:4]1[N:12]=[C:11]([N:13]2[C:17]3[CH:18]=[C:19]([F:22])[CH:20]=[CH:21][C:16]=3[N:15]=[CH:14]2)[N:10]=[C:9]2[C:5]=1[NH:6][C:7](=[O:30])[N:8]2[C@H:23]1[CH2:28][CH2:27][C@H:26]([OH:29])[CH2:25][CH2:24]1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[F:22][C:19]1[CH:20]=[CH:21][C:16]2[N:15]=[CH:14][N:13]([C:11]3[N:10]=[C:9]4[C:5]([NH:6][C:7](=[O:30])[N:8]4[C@H:23]4[CH2:28][CH2:27][C@H:26]([OH:29])[CH2:25][CH2:24]4)=[C:4]([OH:1])[N:12]=3)[C:17]=2[CH:18]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 178518646HCID 178518646, compound

Product 1

HCID 178518662HCID 178518662, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

An oven dried vial containing a stirbar was charged with Pd2 dba3 (2 mg, 0.002 mmol, 0.02 equiv.), 2-di-t-butylphosphino-2′,4′,6′-tri-isopropyl-1,1′-diphenyl (Strem, 3.5 mg, 0.008 mmol, 0.08 equiv.), KOH (17 mg, 0.3 mmol, 3 equiv.) and 6-chloro-2-(6-fluoro-1H-benzo[d]imidazol-1-yl)-9-(trans-4-hydroxycyclohexyl)-7H-purin-8(9H)-one (40 mg, 0.1 mmol, 1 equiv.), followed by 1,4-dioxane (0.3 mL) and degassed water (0.3 mL). A stream of argon was passed through the reaction mixture for 3 min; the vial was then closed and heated at 100° C. After 16 h, the reaction was found to be complete. Preparative HPLC chromatography provided, after evaporation of solvent, the desired product as a white solid. 1H NMR (300 MHz, CD3OD+CDCl3) δ, ppm: 9.04 (s, 1H), 8.45 (dd, 1H), 7.80-7.65 (m, 1H), 7.15-7.08 (m, 1H), 4.42-4.30 (m, 1H), 3.84-3.77 (m, 1H), 2.70-2.60 (m, 2H), 2.25-2.11 (m, 2H), 1.97-1.83 (m, 2H), 1.62-1.40 (m, 2H); MS (EI) m/z 385.3 (MH)+.

Workup

  1. customAn oven dried vial
  2. additioncontaining a stirbar
  3. customdegassed water (0.3 mL)
  4. customthe vial was then closed
  5. waitAfter 16 h
  6. customPreparative HPLC chromatography provided
  7. customafter evaporation of solvent

Sources & evidence

ORD record
ord-419c89f116e9429abea5179c0642980e
Source dataset
uspto-grants-2011_03
Patent number
US07902187B2

Reaction notes

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