Reacción #47914

ord-96d11f32c81e46d482f0855c913c1994

Ecuación de reacción

c1nc2c(c(Nc3ccc4c(c3)OCCO4)n1)CNCC2
5,6,7,8-Tetrahydro-N-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)pyrido[4,3-d]pyrimidin-4-amine
Cc1cccc(B(O)O)c1
m-tolylboronic acid
CCN(CC)CC
triethylamine
Cc1cccc(N2CCc3ncnc(Nc4ccc5c(c4)OCCO5)c3C2)c1
desired compound
Rendimiento 9.6%
Cc1cccc(N2CCc3ncnc(Nc4ccc5c(c4)OCCO5)c3C2)c1
5,6,7,8-Tetrahydro-N-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-6-m-tolylpyrido[4,3-d]pyrimidin-4-amine
Rendimiento 9.6%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Otroof crushed
  2. 2
    Otrothe solvent was removed under vacuum
  3. 3
    OtroThe residue was purified

Procedimiento

5,6,7,8-Tetrahydro-N-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)pyrido[4,3-d]pyrimidin-4-amine (110 mg, 0.39 mmol) was dissolved in anhydrous THF (2 mL). To the mixture was added m-tolylboronic acid (105 mg, 0.78 mmol), Cu(OAc)2 (141 mg, 0.78 mmol) and triethylamine (0.68 g, 0.095 mL) and 390 mg of crushed, activated 4 A molecular seives. The mixture was agitated for 6 h and the solvent was removed under vacuum. The residue was purified using a gradient of ethyl acetate:hexane (0-100%) to give the desired compound as reddish powder (14 mg, 9.6%).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07745451B2uspto-grants-2010_06