HCID 18440372, compound → HCID 18440379, compound

HRID 457697Notes

Reaction equation

HRID 457697 reaction equation
[C:1]1([CH2:7][CH2:8][O:9][C:10]2[N:18]=[C:17]3[C:13]([N:14]=[C:15]([C:21]4[O:22][CH:23]=[CH:24][CH:25]=4)[N:16]3[CH2:19][CH3:20])=[C:12]([NH2:26])[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H][H]>C(O)(C)C.Cl.[OH-].[OH-].[Pd+2]>[C:1]1([CH2:7][CH2:8][O:9][C:10]2[N:18]=[C:17]3[C:13]([N:14]=[C:15]([CH:21]4[CH2:25][CH2:24][CH2:23][O:22]4)[N:16]3[CH2:19][CH3:20])=[C:12]([NH2:26])[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 2

HCID 18440372HCID 18440372, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18440379HCID 18440379, compoundYield 47%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 9942167Palladium hydroxideCatalystHCID 3776IsopropanolSolvent

Procedure

To a solution of 2-(2-phenylethoxy)-8-(furan-2-yl)-9-ethyl-9H-purin-6-ylamine (150 mg, 0.43 mmol) in 45 mL of isopropanol and 2 drops of concentrated HCl was added 150 mg of Pd(OH)2, and the mixture was shaken with hydrogen at 170 psi and 65° C. for 7 hours. The catalyst was filtered off, washed with warm methanol, and the filtrate was concentrated to dryness. The residue was flash chromatographed on a silica gel column eluting with cyclohexane, -EtOAc-CH3OH (60:33:7) to give 2-(2-phenylethoxy)-8-(tetrahydrofuran-2-yl)-9-ethyl-9H-purin-6-ylamine (71 mg, 47%) as chromatographically pure solid: mp 121–123° C.; 1H NMR (Me2SO-d6) δ 1.33 (t, 3H, J=7.1 Hz, CH2CH3), 1.87–2.30 (m, 3H, H-3-Fur and H-4-Fur), 2.55–2.75 (m, 1H, H-3-Fur), 3.02 (t, 2H, J=6.9 Hz, CH2CH2Ph), 3.83 (m, 2H, H-5-Fur), 4.15 (q, 2H, J=7.1 Hz, CH2CH3), 4.41 (t, 2H, J=6.9 Hz, CH2CH2Ph), 5.14 (t, 1H, J=6.6 Hz, H-2-Fur), 7.17–7.40 (m, 7H, H-Ph and NH2). Anal. (C19H23N5O2) C, H, N.

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed with warm methanol
  3. concentrationthe filtrate was concentrated to dryness
  4. customchromatographed on a silica gel column
  5. washeluting with cyclohexane

Sources & evidence

ORD record
ord-2d363748381a4f78bb48969ebade46c8
Source dataset
uspto-grants-2007_03
Patent number
US07189730B2

Reaction notes

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