7H-Pyrrolo(2,3-d)pyrimidine-5-carbonitrile, 4-amino-7-((2-hydroxyethoxy)methyl)- → Methyl 4-amino-7-[(2-hydroxyethoxy)methyl]-7H-pyrrolo[2,3-d]pyrimidine-5-carboximidate

Participants

Reaction Steps

Methyl 4-amino7-(2-hydroxyethoxymethyl)pyrrolo[2,3-d]-pyrimidine-5-formimidate was prepared by first dissolving compound (17a) (0.5 g; 2.15 mmole) in dry MeOH (15 ML). A sodium methoxide (1 M) solution (5 mL) was added and the mixture was stirred at room temperature for 3 hours. This solution was adjusted to pH7 by adding small portions of Dowex 50 (H+ form, prewashed with dry CH3OH). The solution was then quickly filtered to remove the ion-exchange resin followed by concentration of the filtrate in vacuo to a semisolid mass. The residue was purified by a column (2×60 cm; prepacked in CH2Cl2) of silica gel (15 g; 60-200 mesh). Elution of the column with CH2Cl2 :CH3OH (96:4, V:V) afforded the desired nucleoside which was crystallized from dry CH3OH-ET2O to afford the pure imidate (0.13 g; yield 23%); mp. 124° C.; IR (KBr)γ3350 (OH) and 1600 cm-1 ; UVλmax nm:(pH 1), 237 (14700) 280 (12710); (MeOH), 278 (15770); (pH 11), 217 (26100) 278 (13880). 1H NMR (DMSO-d6): δ3.50 (nm, 4, CH2), 3.75 (s, 3, OCH3), 5.58 (s, 2, C1 ''CH2), 7.25 (brs 1, NH2), 7.75 (s, 1, C6 --H), 8.06 (s, 1, C2 --H), 8.20 (brs, 1, C=NH, 9.98 (brs,1,NH2). Anal. (C11H15N5O3) C,H,N.

Provenance & Evidence