Triphenylphosphine → HCID 18950603, compound

HRID 1492640Notes

Reaction equation

HRID 1492640 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.[CH3:34][C:35]1[N:40]=[C:39]2[N:41]=[C:42]([CH2:44][CH3:45])[NH:43][C:38]2=[C:37]([CH3:46])[CH:36]=1.[Cl:47][C:48]1[CH:65]=[C:64]([CH2:66]O)[CH:63]=[C:62]([CH2:68][CH:69]=[CH2:70])[C:49]=1[O:50][CH:51]([C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1)[C:52]([O:54][CH3:55])=[O:53]>C1COCC1>[C:52]([CH:51]([C:56]1[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=1)[O:50][C:49]1[C:62]([CH2:68][CH:69]=[CH2:70])=[CH:63][C:64]([CH2:66][N:41]2[C:39]3=[N:40][C:35]([CH3:34])=[CH:36][C:37]([CH3:46])=[C:38]3[N:43]=[C:42]2[CH2:44][CH3:45])=[CH:65][C:48]=1[Cl:47])([O:54][CH3:55])=[O:53]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 98153742,6-Dimethyl-8-ethyl-1-deazapurineHCID 18950593HCID 18950593, compound

Product 1

HCID 18950603HCID 18950603, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a magnetically stirred solution of 0.541 g (2.06 mmol) of triphenylphosphine in 4 mL anhydrous THF was added 406 μL (2.06 mmol) of diisopropylazodicarboxylate at -20° C. The reaction mixture was stirred for 1 hour, followed by addition of a solution of 0.301 g (1.72 mmol) of 5,7-dimethyl-2-ethylimidazo[4,5-b]pyridine and 0.596 g (1.72 mmol) of the product of Step C in 6 mL THF. The reaction mixture was stirred 20 min at -20° C., then warmed to room temperature and stirred an additional 1 hour. The reaction mixture was then evaporated in vacuo and applied to a silica gel flash chromatography column. Elution with 50% EtOAc-hexane, evaporation of the purified fractions and drying in vacuo afforded 0.440 g (51%) of the title compound.

Workup

  1. stirringThe reaction mixture was stirred 20 min at -20° C.
  2. stirringstirred an additional 1 hour
  3. customThe reaction mixture was then evaporated in vacuo
  4. washElution
  5. customwith 50% EtOAc-hexane, evaporation of the purified fractions
  6. customdrying in vacuo

Sources & evidence

ORD record
ord-39926b21169b497c987b16fc17bbc52c
Source dataset
uspto-grants-1994_12
Patent number
US05374638

Reaction notes

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