Triphenylphosphine → HCID 59395463, compound

HRID 1097718

Reaction equation

HRID 1097718 reaction equation
[CH2:1]([N:5]1[C:13]2[N:12]=[C:11]([Cl:14])[N:10](CC=C)[C:9]=2[C:8](=[O:18])[NH:7][C:6]1=[O:19])[CH2:2][CH2:3][CH3:4].[C:20]1([C:26]2[CH:30]=[C:29]([CH2:31][CH2:32][CH2:33][CH2:34]O)[O:28][N:27]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.N(C(OCC1C=CC=CC=1)=O)=NC(OCC1C=CC=CC=1)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[CH2:1]([N:5]1[C:13]2[N:12]=[C:11]([Cl:14])[NH:10][C:9]=2[C:8](=[O:18])[N:7]([CH2:34][CH2:33][CH2:32][CH2:31][C:29]2[O:28][N:27]=[C:26]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:30]=2)[C:6]1=[O:19])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 755571,2-Bis(phenylmethyl) 1,2-diazenedicarboxylateHCID 59299582HCID 59299582, compoundHCID 59395604HCID 59395604, compound

Product 1

HCID 59395463HCID 59395463, compoundYield 35.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

3-Butyl-8-chloro-7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dione (100 mg, 0.354 mmol) and 4-(3-phenyl-5-isoxazolyl)-1-butanol (77 mg, 0.355 mmol) were dissolved in dry THF (4 ml) under nitrogen. A solution of dibenzyl azodicarboxylate (94%, 224 mg, 0.708 mmol) in dry THF (2 ml) was added. The mixture was cooled to 0° C. and a solution of triphenylphosphine (185 mg, 0.708 mmol) in dry THF (1 ml) was added. The mixture was stirred for 20 min at 0° C. then at room temperature overnight. The mixture was degassed then stirred with morpholine (0.308 ml) and tetrakis(triphenylphosphine)palladium(0) (82 mg) for 4.5 h. A further 60 mg of tetrakis(triphenylphosphine)palladium(0) was added and stirring continued overnight. The reaction was worked up by partition between EtOAc and 2M HCl, the organic phase evaporated and purified by aminopropyl SPE (5 g) washing with THF-MeOH (1:1), MeOH and eluting with DCM-MeOH (1:1) containing 5% AcOH. Further purification by MDAP afforded the title compound (56 mg).

Workup

  1. customat room temperature
  2. customovernight
  3. customThe mixture was degassed
  4. stirringthen stirred with morpholine (0.308 ml) and tetrakis(triphenylphosphine)palladium(0) (82 mg) for 4.5 h
  5. additionA further 60 mg of tetrakis(triphenylphosphine)palladium(0) was added
  6. stirringstirring continued overnight
  7. customby partition between EtOAc and 2M HCl
  8. customthe organic phase evaporated
  9. custompurified by aminopropyl SPE (5 g)
  10. washwashing with THF-MeOH (1:1), MeOH
  11. washeluting with DCM-MeOH (1:1)
  12. additioncontaining 5% AcOH
  13. customFurther purification by MDAP

Sources & evidence

ORD record
ord-1b6ecf0713db43e3a1daa254858a9817
Source dataset
uspto-grants-2012_03
Patent number
US08143264B2

Linked notes

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