Triethylamine → HCID 68157269, compound

HRID 243272Notes

Reaction equation

HRID 243272 reaction equation
Cl.[F:2][C:3]1[CH:4]=[CH:5][C:6]2[N:10]=[C:9]([CH2:11][NH2:12])[N:8]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:7]=2[CH:19]=1.Cl[C:21]1[N:29]=[CH:28][N:27]=[C:26]2[C:22]=1[N:23]=[CH:24][N:25]2[CH:30]1[CH2:35][CH2:34][CH2:33][CH2:32][O:31]1.C(N(CC)CC)C>C(O)(C)C>[F:2][C:3]1[CH:4]=[CH:5][C:6]2[N:10]=[C:9]([CH2:11][NH:12][C:21]3[N:29]=[CH:28][N:27]=[C:26]4[C:22]=3[N:23]=[CH:24][N:25]4[CH:30]3[CH2:35][CH2:34][CH2:33][CH2:32][O:31]3)[N:8]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:7]=2[CH:19]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 977406-chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purineHCID 68157878HCID 68157878, compound

Product 1

HCID 68157269HCID 68157269, compoundYield 70.5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

(6-Fluoro-1-phenyl-1H-benzoimidazol-2-yl)methylamine hydrochloride (0.113 g, 0.4 mmol), 6-chloro-9-(tetrahydropyran-2-yl)-9H-purine (0.19 g, 0.8 mmol), triethylamine (0.28 mL, 2 mmol) in isopropanol (2 mL) was heated to 80° C. in a sealed tube for 6 h. The reaction mixture was partitioned between DCM and water and the organic layer was dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-3.5% MeOH in DCM) to afford the title compound as a colourless gum, (0.125 g, 70%). LCMS (Method B): RT 2.99 min [M+H]+ 444.19.

Workup

  1. customThe reaction mixture was partitioned between DCM and water
  2. dry with materialthe organic layer was dried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customThe resulting residue was purified by column chromatography (Si—PCC, gradient 0-3.5% MeOH in DCM)

Sources & evidence

ORD record
ord-acacfad07cfa48d895ed637c5eb3486d
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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