Tetrabutylammonium Fluoride → 1,5-Naphthyridine

HRID 1587831Notes

Reaction equation

HRID 1587831 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si](OCCO[C:40]1[N:41]=[C:42]2[C:47](=[CH:48][CH:49]=1)[N:46]=[C:45](CC)[CH:44]=[C:43]2OCC1C=CC(C2C=CC=CC=2C2N=NN(C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)N=2)=CC=1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1>C1COCC1>[N:41]1[C:42]2[C:47](=[N:46][CH:45]=[CH:44][CH:43]=2)[CH:48]=[CH:49][CH:40]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 53976296HCID 53976296, compound

Product 1

HCID 1360701,5-NaphthyridineYield 550.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
40 °C

Procedure

A 1M solution of tetrabutylammonium fluoride in THF (14 ml) was added to a solution of compound E (1.1 g) in THF (10 ml) and the mixture was stirred for 2 hours. The solution was then warmed to 40° C. for 10 minutes. Volatile material was removed by evaporation and the residual oil was dissolved in ethyl acetate (75 ml) and washed with water (75 ml and 30 ml). The precipitated solid was collected by filtration to give 2-ethyl-6-hydroxy-4-[(2'-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl)-methoxy]-1,5-naphthyridine (F) (0.83 g) as a white solid, m.p. 148°-149° C.; NMR (d6 -DMSO): 1.2(t,3H), 2.7(q,2H), 5.3(s,2H), 6.65-7.9(m,26H), 11.1(s,1H).

Workup

  1. customVolatile material was removed by evaporation
  2. dissolutionthe residual oil was dissolved in ethyl acetate (75 ml)
  3. washwashed with water (75 ml and 30 ml)
  4. filtrationThe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-b895d3e606f14bfa9666ce126eb04785
Source dataset
uspto-grants-1993_06
Patent number
US05219863

Reaction notes

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