Ethanol → 1H-Pyrazolo(3,4-d)pyrimidine

반응식

CN1CCOCC1.ClC(OCC(C)C)=O.N[C:17]1[C:25]2[C:20](=[N:21][CH:22]=[N:23][C:24]=2NC2C=CC=C(Cl)C=2)[NH:19][N:18]=1.C(O)C>C1COCC1.CS(C)=O>[NH:19]1[C:20]2=[N:21][CH:22]=[N:23][CH:24]=[C:25]2[CH:17]=[N:18]1

참가 물질

실험 절차

Analogously to Example 5, 436 mg (2.3 mmol) of N-ethoxycarbonyl-(D/L)-valine [prepared from (D/L)-valine as described in J. Org. Chem. 60, 7256 (1995)] in 4.8 ml of THF and 506 μl (4.6 mmol) of NMM are activated with 349 μl (2.6 mmol) of isobutyl chloroformate and then reacted with 600 mg (2.3 mmol) of 3-amino-4-(3-chloro-phenylamino)-1H-pyrazolo[3,4-d]pyrimidine (see Step 1.6). Dissolution in DMSO (2 ml) at 100° C., addition of 25 ml of ethanol and cooling yield rac.-4-(3-chloro-phenylamino)-3{N-ethoxycarbonyl-valyl)-amino}-1H-pyrazolo[3,4-d]pyrimidine; HPLC: tRet(grad20-100/20)=13.2; FAB-MS: (M+H)+=432.