Ethanol → HCID 18440366, compound

HRID 457698Notes

Reaction equation

HRID 457698 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](Br)[N:16]3[CH2:19][CH3:20])=[C:12]([NH2:22])[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].[CH2:25]([OH:27])[CH3:26]>>[C:1]1([CH2:7][CH2:8][O:9][C:10]2[N:18]=[C:17]3[C:13]([N:14]=[C:15]([O:27][CH2:25][CH3:26])[N:16]3[CH2:19][CH3:20])=[C:12]([NH2:22])[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 10237126HCID 10237126, compound

Product 1

HCID 18440366HCID 18440366, compoundYield 52%

Conditions

Temperature
85 °C

Procedure

To a suspension of 2-(2-phenylethoxy)-8-bromo-9-ethyl-9H-purin-6-ylamine (145 mg, 0.4 mmol) and dry NaOH (80 mg, 2.0 mmol) was added ethanol (25 mL). This mixture was heated at 85° C. for 7 hours. The solvent was removed under reduced pressure and the residue was neutralized with 2N HCl and extracted with CHCl3. The organic layer was dried (Na2SO4) and concentrated in vacuo. The residue was recrystallized from acetonitrile to give 2-(2-phenylethoxy)-8-ethoxy-9-ethyl-9H-purin-6-ylamine (68 mg, 52%) as a white solid: mp 161–164° C.; 1H NMR (Me2SO-d6) δ 1.26 (t, 3H, J=7.1 Hz, OCH2CH3), 1.33 (t, 3H, J=7.0 Hz, NCH2CH3), 3.00 (t, 2H, J=6.9 Hz, CH2CH2Ph), 3.88 (q, 2H, J=7.1 Hz, OCH2CH3), 4.38 (t, 2H, J=6.9 Hz, CH2CH2Ph), 4.48 (q, 2H, J=7.0 Hz, NCH2CH3), 6.79 (s, 2H, NH2), 7.18–7.36 (m, 5H, H-Ph). Anal. (C17H21N5O2) C, H, N.

Workup

  1. customThe solvent was removed under reduced pressure
  2. extractionextracted with CHCl3
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-af30588d198e4702a399785116976b8a
Source dataset
uspto-grants-2007_03
Patent number
US07189730B2

Reaction notes

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