Reaktion #1726426

Reaktionsgleichung

diethyl N-[4-{1-(tetrahydropyr-2-yloxy)-3-(2-pivaloylamino-4-hydroxypyrido[2,3-d]pyrimidin-6-yl)prop-2-en-2-yl}benzoyl]glutamate

→

diethyl N-[4-{1-(tetrahydropyr-2-yloxy)-3-(2-pivaloylamino-4-hydroxy-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-6-yl)prop-2-yl}benzoyl]glutamate

Ausbeute 68.0%

Lösungsmittel

methanol

acetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationfiltered through Celite
2. 2
   EinengenThe filtrate was concentrated
3. 3
   workup.ADDITIONdiluted with ethyl acetate
4. 4
   SonstigeThe solid which formed
5. 5
   Temperaturafter cooling for 15 hour
6. 6
   Filtrationwas collected by filtration
7. 7
   Waschenwashed with cold ethyl acetate
8. 8
   Sonstigedried

Vorschrift

A solution of 1.16 g (1.68 mm) of diethyl N-[4-{1-(tetrahydropyr-2-yloxy)-3-(2-pivaloylamino-4-hydroxypyrido[2,3-d]pyrimidin-6-yl)prop-2-en-2-yl}benzoyl]glutamate and 174 mg (20%) of amorphous platinum (IV) oxide in 150 ml of glacial acetic acid was hydrogenated for 10 hours at 50 psi. The reaction mixture was diluted with 50 ml of methanol and filtered through Celite. The filtrate was concentrated and diluted with ethyl acetate. The solid which formed after cooling for 15 hour was collected by filtration, washed with cold ethyl acetate and dried to give 700 mg (68%) of diethyl N-[4-{1-(tetrahydropyr-2-yloxy)-3-(2-pivaloylamino-4-hydroxy-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-6-yl)prop-2-yl}benzoyl]glutamate. mp 183°-186° C. Analysis calculated for C36H51O9N5 : C, 61.95; H, 7.37; N, 10.04. Found: C, 62.00; H, 7.17; N, 9.83. NMR (CDCL3), delta, 1.23 (t, 3H, J=7 Hz), 1.26 (s, 9H), 1.32 (t, 3H, J=7 Hz), 2.26-2.82 (m, 9H), 2.06-2.12 (m, 2H), 2.26-2.38 (m, 1H), 2.43-2.58 (m, 2H), 2.62-2.83 (m, 1H), 2.84-3.10 (m, 2H) 3.12-3.21 and 2.32-3.40 (m, m, 1H), 3.41-3.52 (m, 2H), 3.68-3.92 (m, 2H), 4.13 (q, 2H, J=7 Hz), 4.25 (q, 2H, J=7 Hz), 4.44-4.63 (m, 2H, CH, NH), 4.78-4.84 (m, 1H) 7.02 (brd, 1H, NH, J=7.1 Hz), 7.29 (brs, NH), 7.31-7.37 (m, 2H), 7.75-7.78 (m, 2H), 11.20 (brs, NH).

Quelle