7-Deazaadenine

To a suspension of compound 1 (1.0 g, 6.0 mmol) in water (50 mL) was added Raney nickel (3.0 g). The reaction mixture was heated at reflux for 4 h, and then the hot solution was filtered through celite. The nickel residue was washed with water (100 mL). The combined aqueous filtrate was evaporated to dryness to yield the product (0.7 g, 87.5percent).To a solution of 200 mg (1.49 mmol) of 7H-pyrrolo[2, 3-d]pyrimidin-4-amine in 4 mL of DMF, 235 muL of dimethylformamide dimethyl acetal were added. The mixture was stirred at room temperature overnight. The solvent was then removed in vacuo and the residue taken up with DCM, washed with brine, dried over anhydrous Na2SO4and evaporated to dryness. The crude was triturated with diisopropylether and filtered, to afford 204 mg (73%) of the title compound. 1H NMR (600 MHz, DMSO-cie) delta ppm 3.10 (s, 3 H) 3.16 (s, 3 H) 6.45 (dd, J=3.39, 1.92 Hz, 1 H) 7.21 (dd, J=3.11 , 2.38 Hz, 1 H) 8.28 (s, 1 H) 8.79 (s, 1 H) 11.60 (br. s., 1 H) HRMS (ESI) calcd for C9HnN5 [M+H]+ 190.1087, found 190.1085.Solid K2CO3 (0.930 g, 6.71 mmol, 3.0 equiv) was added to a stirringsolution of 7H-pyrrolo[2, 3-d]pyrimidin-4-amine 16 (0.300 g, 2.24 mmol, 1.0 equiv) in dry DMF (15 mL) at room temperature. After 1 h, a solution of tert-butyl (2-chloroethyl)carbamate (0.602 g, 3.35 mmol, 1.5 equiv) in dry DMF (5 mL) was added dropwise. Theresulting suspensionwas stirred for 48 h at 80 C. After the reactionwas complete, as indicated by TLC, the crude material was filteredthrough a plug of Celite to remove inorganic salts and thenwashedwith dichloromethane (50 mL x 4). The filtratewas concentrated byrotary evaporation and purification was carried out using 9%methanol/dichloromethane as the eluent to provide a light brownsolid of the corresponding tert-butyl carbamate. This material wasdissolved in 15 mL of a 1:1 (v/v) mixture of trifluoroacetic acid anddichloromethane. The resulting solution was stirred at room temperaturefor 4 h before it was concentrated by rotary evaporation at35 C. The resulting trifluoroacetic acid salt of the deprotectedamine was dissolved in absolute ethanol (20 mL) and stirred withAmberlyst A-21 free base resin (4 g) at room temperature for 10 h.The heterogeneous reaction mixture was filtered and washed withmethanol (50 mL x 4) until the chromophorewas no longer evidentin the drippingwash by TLC. The filtratewas concentrated by rotaryevaporation and purified using 15% ammonia-saturated methanol/dichloromethane as the eluent to provide product D as a lightbrown solid in 58% yield (0.231 g, 1.30 mmol) from 16. m.p.145e146 C; 1H NMR (DMSO-d6, 500 MHz): d 8.03 (1H, s), 7.14 (1H, d, J 3.4 Hz), 6.90 (2H, br, s), 6.50 (1H, d, J 3.4 Hz), 4.07 (2H, t, J 6.6 Hz), 2.86 (2H, t, J 6.6 Hz), 1.57 (2H, br, s); 13C NMR(DMSO-d6, 125 MHz): d 157.37, 151.40, 149.55, 124.38, 102.35, 98.07, 47.16, 41.99; HRMS: m/z calcd for C8H11N5, 177.1014; found 177.1010.

Molecular Weight:134.14
XLogP3:0.3
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Exact Mass:134.059246208
Monoisotopic Mass:134.059246208
Topological Polar Surface Area:67.6
Heavy Atom Count:10
Complexity:127
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes