Morpholine → HCID 59395644, compound

HRID 1097722Notes

Reaction equation

HRID 1097722 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][C:19]3[O:23][N:22]=[C:21]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=4)[N:20]=3)[C:6](=[O:30])[NH:5][C:4]=2[N:3]=1.C(=O)([O-])[O-].[K+].[K+].I[CH2:38][CH2:39][CH3:40].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][CH2:18][C:19]3[O:23][N:22]=[C:21]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=4)[N:20]=3)[C:6](=[O:30])[N:5]([CH2:38][CH2:39][CH3:40])[C:4]=2[N:3]=1

Participants

7

Reactant 4

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 336431-IodopropaneHCID 59395815HCID 59395815, compound

Product 1

HCID 59395644HCID 59395644, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

A solution of 8-chloro-7-(2-propen-1-yl)-1-{4-[3-(2-pyridinyl)-1,2,4-oxadiazol-5-yl]butyl}-3,7-dihydro-1H-purine-2,6-dione (40 mg, 0.09 mmol) in DMF (3 ml) was treated with potassium carbonate (15 mg, 0.11 mmol) and 1-iodopropane (19 mg, 0.11 mmol). The mixture was heated at 40° C. for 3 h then at 70° C. for a further 3 h. The mixture was cooled and degassed by the successive application of vacuum and nitrogen gas. The mixture was then treated with a solution of tetrakis(triphenylphosphine)palladium(0) (10 mg, 0.009 mmol) and morpholine (0.1 ml, 1.2 mmol) and then stirred overnight. The mixture was evaporated and partitioned between chloroform (2 ml) and water (2 ml). The aqueous phase was extracted with further chloroform (2 ml) and the combined organics evaporated and the residue dissolved in methanol (2 ml). The solution was applied to a 1 g aminopropyl SPE and eluted with methanol and then with 5% acetic acid in methanol. Product-containing fractions were pooled and evaporated and the product further purified by MDAP to reveal 8-chloro-3-propyl-1-{4-[3-(2-pyridinyl)-1,2,4-oxadiazol-5-yl]butyl}-3,7-dihydro-1H-purine-2,6-dione (1.4 mg) as a white solid.

Workup

  1. temperatureThe mixture was cooled
  2. customdegassed by the successive application of vacuum and nitrogen gas
  3. customThe mixture was evaporated
  4. custompartitioned between chloroform (2 ml) and water (2 ml)
  5. extractionThe aqueous phase was extracted with further chloroform (2 ml)
  6. customthe combined organics evaporated
  7. dissolutionthe residue dissolved in methanol (2 ml)
  8. washeluted with methanol
  9. customevaporated
  10. customthe product further purified by MDAP

Sources & evidence

ORD record
ord-5f3c473edc93402483e73afc8247e473
Source dataset
uspto-grants-2012_03
Patent number
US08143264B2

Reaction notes

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