Morpholine → HCID 59395545, compound

HRID 1097724Notes

Reaction equation

HRID 1097724 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][CH2:18][N:19]3[CH2:23][CH2:22][CH:21]([CH2:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[C:20]3=[O:31])[C:6](=[O:32])[N:5]([CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[C:4]=2[N:3]=1.N1CCOCC1>C1COCC1.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][CH2:18][N:19]3[CH2:23][CH2:22][CH:21]([CH2:24][C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)[C:20]3=[O:31])[C:6](=[O:32])[N:5]([CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[C:4]=2[N:3]=1

Participants

5

Reactant 2

HCID 8083MorpholineHCID 59395380HCID 59395380, compound

Product 1

HCID 59395545HCID 59395545, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 8-chloro-1-{4-[2-oxo-3-(phenylmethyl)-1-pyrrolidinyl]butyl}-3-pentyl-7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dione (0.35 g, 0.67 mmol), Pd(PPh3)4 (0.082 g, 0.07 mmol) and morpholine (0.6 ml, 6.7 mmol) in THF (10 ml) was degassed (sequential evacuation followed by addition of nitrogen×3) then stirred for 4 h. The solution was then loaded onto an aminopropyl SPE (5 g) and eluted first with MeOH then 5% AcOH/MeOH to provide the title compound containing a small impurity. Further purification over silica (10 g SPE, gradient elution ether/ethyl acetate 1:0 to 0:1) provided the title compound as a clear oil (0.10 g, 31%).

Workup

  1. addition(sequential evacuation followed by addition of nitrogen×3)
  2. washeluted first with MeOH

Sources & evidence

ORD record
ord-6717b059a8e44a939c424b94bdb40dfa
Source dataset
uspto-grants-2012_03
Patent number
US08143264B2

Reaction notes

Loading…