Sodium hydride → HCID 13210503, Verbindung

To a mixture of 372 mg of sodium hydride (purity 50%) and 30 ml of N,N-dimethylformamide was added dropwise a solution of 3 g of 1-benzyl-4-[4-(2-pyrimidinylamino)benzyl]-2,3-dioxopiperazine in 20 ml of N,N-dimethylformamide with stirring over 30 min., after which the resulting mixture was subjected to reaction at 60° to 70° C. for one hour. After the completion of the reaction, 1.3 g of pivaloyloxymethyl chloride was dropped thereinto over 10 min. at the same temperature. After the completion of the dropwise addition, the resulting mixture was subjected to reaction at 70° to 80° C. for 30 min. After the completion of the reaction, the solvent was removed by distillation under reduced pressure, and the residue thus obtained was extracted with 100 ml of chloroform. The chloroform layer was washed with 30 ml of water and 40 ml of saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate, after which the solvent was removed by distillation under reduced pressure. The residue thus obtained was purified by column chromatography (Wakogel C-200, eluted with chloroform), and then recrystallized from ethyl acetate-diisopropyl ether, to obtain 2.5 g (64.3% yield) of 1-benzyl-4-{4-[N-pivaloyloxymethyl-N-(2-pyrimidinyl)amino]benzyl}-2,3-dioxopiperazine having a melting point of 144° to 146° C.

1. customafter which the resulting mixture was subjected to reaction at 60° to 70° C. for one hour
2. additionwas dropped
3. waitover 10 min. at the same temperature
4. additionAfter the completion of the dropwise addition
5. customthe resulting mixture was subjected to reaction at 70° to 80° C. for 30 min
6. customAfter the completion of the reaction
7. customthe solvent was removed by distillation under reduced pressure
8. customthe residue thus obtained
9. extractionwas extracted with 100 ml of chloroform
10. washThe chloroform layer was washed with 30 ml of water and 40 ml of saturated aqueous sodium chloride solution in this order
11. dry with materialdried over anhydrous magnesium sulfate
12. customafter which the solvent was removed by distillation under reduced pressure
13. customThe residue thus obtained
14. customwas purified by column chromatography (Wakogel C-200, eluted with chloroform)
15. customrecrystallized from ethyl acetate-diisopropyl ether

ORD-Eintrag

ord-c92f8ae6bc064a59bde1fe992f23a11c

Quelldatensatz

uspto-grants-1984_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US04459407