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

HRID 1097650

Reaction equation

HRID 1097650 reaction equation
[C:1]1([CH2:7][C:8]2[N:12]=[C:11]([CH2:13][CH2:14][CH2:15]O)[O:10][N:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:17][C:18]1[N:26](CC=C)[C:25]2[C:24](=[O:30])[NH:23][C:22](=[O:31])[N:21]([CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[C:20]=2[N:19]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(COC(/N=N/C(OCC2C=CC=CC=2)=O)=O)=CC=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:17][C:18]1[NH:26][C:25]2[C:24](=[O:30])[N:23]([CH2:15][CH2:14][CH2:13][C:11]3[O:10][N:9]=[C:8]([CH2:7][C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[N:12]=3)[C:22](=[O:31])[N:21]([CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[C:20]=2[N:19]=1

Participants

8

Reactant 5

HCID 8083MorpholineHCID 11776TriphenylphosphineHCID 5387121Dibenzyl azodicarboxylateHCID 592995577-Allyl-8-chloro-3-pentyl-1H-purine-2,6(3H,7H)-dioneHCID 593955733-[3-(Phenylmethyl)-1,2,4-oxadiazol-5-yl]-1-propanol

Product 1

HCID 593957888-Chloro-3-pentyl-1-(3-[3-(phenylmethyl)-1,2,4-oxadiazol-5-yl]propyl)-3,7-dihydro-1H-purine-2,6-dione

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-[3-(phenylmethyl)-1,2,4-oxadiazol-5-yl]-1-propanol (88 mg, 0.4 mmol) in THF (4 ml) was treated with 8-chloro-3-pentyl-7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dione (100 mg, 0.34 mmol) and PPh3 (115 mg, 0.44 mmol) under nitrogen. DBAD (101 mg, 0.44 mmol) was added in one portion and the reaction left to react for 5 h. The mixture was degassed by applying a vacuum and then nitrogen was introduced. Pd(PPh3)4 (39 mg, 0.034 mmol) was added and the mixture degassed once more. Morpholine (294 μl, 3.4 mmol) was added and the mixture was stirred under nitrogen for 3 h. The mixture was partitioned between 2M HCl (aq) and EtOAc. The organic layer was separated, washed with brine, dried (MgSO4) and concentrated. The title compound was obtained as a white solid after purification by MDAP (64 mg, 42%).

Workup

  1. waitthe reaction left
  2. customto react for 5 h
  3. customThe mixture was degassed
  4. additionnitrogen was introduced
  5. customthe mixture degassed once more
  6. customThe mixture was partitioned between 2M HCl (aq) and EtOAc
  7. customThe organic layer was separated
  8. washwashed with brine
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-b15438e57bd24b7aaab077db1851457d
Source dataset
uspto-grants-2012_03
Patent number
US08143264B2

Linked notes

Loading…