Morpholine → 8-Chloro-1-(3-{3-[(4-chlorophenyl)methyl]-1,2,4-oxadiazol-5-yl}propyl)-3-pentyl-3,7-dihydro-1H-purine-2,6-dione

HRID 1097651Notes

Reaction equation

HRID 1097651 reaction equation
[Cl:1][C:2]1[N:10](CC=C)[C:9]2[C:8](=[O:14])[N:7]([CH2:15][CH2:16][CH2:17][C:18]3[O:22][N:21]=[C:20]([CH2:23][C:24]4[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=4)[N:19]=3)[C:6](=[O:31])[N:5]([CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[C:4]=2[N:3]=1.N1CCOCC1>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:1][C:2]1[NH:10][C:9]2[C:8](=[O:14])[N:7]([CH2:15][CH2:16][CH2:17][C:18]3[O:22][N:21]=[C:20]([CH2:23][C:24]4[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=4)[N:19]=3)[C:6](=[O:31])[N:5]([CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[C:4]=2[N:3]=1

Participants

5

Reactant 2

HCID 8083MorpholineHCID 593957228-chloro-1-(3-{3-[(4-chlorophenyl)methyl]-1,2,4-oxadiazol-5-yl}propyl)-3-pentyl-7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dione

Product 1

HCID 593955258-Chloro-1-(3-{3-[(4-chlorophenyl)methyl]-1,2,4-oxadiazol-5-yl}propyl)-3-pentyl-3,7-dihydro-1H-purine-2,6-dione

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 8-chloro-1-(3-{3-[(4-chlorophenyl)methyl]-1,2,4-oxadiazol-5-yl}propyl)-3-pentyl-7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dione (0.18 g, 0.34 mmol) in DMF (5 ml) was degassed by sequential evacuation of the flask and admission of nitrogen (×3) and morpholine (0.5 ml, 5.8 mmol), and Pd(PPh3)4 (80 mg, 0.068 mmol) added. The solution was stirred for 72 h then concentrated and the residues loaded onto an aminopropyl SPE (10 g) with MeOH. Elution with MeOH followed by 5% AcOH/MeOH provided the title compound as a pale yellow solid, which was washed with ether to yield a white solid (0.053 g, 32%).

Workup

  1. additionadded
  2. concentrationthen concentrated
  3. washElution with MeOH

Sources & evidence

ORD record
ord-73a5852681eb4fad9da2c012ba2e56a8
Source dataset
uspto-grants-2012_03
Patent number
US08143264B2

Reaction notes

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