Acetic Acid → HCID 178478148, compound

Participants

Reaction Steps

Analogously to Example 32, 521 mg (2.00 mmol) of 3-amino-4-(3-chlorophenylamino)-1H-pyrazolo[3,4-d]pyrimidine and 343 μl of acetic acid are dissolved in 50 ml of methanol and reacted with 523 mg (3.0 mmol) of 2-(tetrazol-5-yl)-benzaldehyde (Step 61.1) to form 4-(3-chloro-phenylamino)-3{[2-(tetrazol-5-yl)-phenyl]-methyleneamino}-1H-pyrazolo[3,4-d]pyrimidine. The above intermediate is reduced in 30 ml of DMEU with 16 ml (16 mmol) of DIBAL-H and the reaction mixture is hydrolyzed analogously. The DMEU solution is poured into water, adjusted to pH=3 with 1 N HCl and extracted with ethyl acetate. The organic phase yields, after washing 10× with water and 1× with brine, drying (Na2SO4), concentration by evaporation and digestion in diethyl ether, 4-(3-chloro-phenylamino)-3-[2-(tetrazol-5-yl)-benzylamino]-1H-pyrazolo-[3,4-d]pyrimidine; TLC: Rf=0.19 (CHCl3/methanol/H2O/acetic acid=85:13:1.5:0.5); HPLC: tRet(grad20-100)=7.7; FAB-MS: (M+H)+=419.

Provenance & Evidence