3-[4-(2,6-Dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[2.2.2]oct-1-yl]-acrylonitrile → 3-[4-(2,6-Dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[2.2.2]oct-1-yl]-propionitrile

HRID 480142Notes

Reaction equation

HRID 480142 reaction equation
[O:1]=[C:2]1[N:10]([CH2:11][CH2:12][CH3:13])[C:9]2[N:8]=[C:7]([C:14]34[CH2:21][CH2:20][C:17]([CH:22]=[CH:23][C:24]#[N:25])([CH2:18][CH2:19]3)[CH2:16][CH2:15]4)[NH:6][C:5]=2[C:4](=[O:26])[N:3]1[CH2:27][CH2:28][CH3:29].[H][H]>CO.C(Cl)Cl.[Pd]>[O:1]=[C:2]1[N:10]([CH2:11][CH2:12][CH3:13])[C:9]2[N:8]=[C:7]([C:14]34[CH2:19][CH2:18][C:17]([CH2:22][CH2:23][C:24]#[N:25])([CH2:20][CH2:21]3)[CH2:16][CH2:15]4)[NH:6][C:5]=2[C:4](=[O:26])[N:3]1[CH2:27][CH2:28][CH3:29]

Participants

6

Reactant 2

HCID 670783823-[4-(2,6-Dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[2.2.2]oct-1-yl]-acrylonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 187677383-[4-(2,6-Dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[2.2.2]oct-1-yl]-propionitrileYield 90.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 3-[4-(2,6-dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[2.2.2]oct-1-yl]-acrylonitrile (110 mg, 0.278 mmol) in MeOH (20 ml) and CH2Cl2 (5 ml) was hydrogenated using Pd on carbon (10 mol %) and a ballon of hydrogen affixed to a 3-way stopcock/ground glass adapter. After stirring overnight, the mixture was degassed, filtered through Celite and concentrated in vacuo to give a brittle foam (100 mg, 90%). 1H NMR (400 MHz, CDCl3); δ 0.93 (coincident triplets, 6H), 1.53 (m, 6H),1.57 (t, 2H), 1.67 (m, 2H), 1.77 (m, 2H), 2.00 (m, 6H), 2.24 (t, 2H), 3.99 (t, 2H), 4.05 (t, 2H), 12.17 (s, 1H).

Workup

  1. customthe mixture was degassed
  2. filtrationfiltered through Celite
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e7b09066b0e64b478f91ae2ce4ce0ead
Source dataset
uspto-grants-2003_11
Patent number
US06649600B1

Reaction notes

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