Sodium Bicarbonate → HCID 178508221, compound

Participants

Reaction Steps

(+)-(1S,2R,4R)-4-(2-Amino-6-chloro-9H-purin-9-yl)-2-(hydroxymethyl)cyclopentanol, (1.70 g, 6.00 mmol) and thiourea (456 mg, 6.00 mmol) were refluxed in water (15 mL) for 1.0 hour. The cooled solution was adjusted to pH5 with saturated aqueous sodium bicarbonate. The resulting precipitate was filtered, washed with water and dried to give title compound as white powder (1.20 g, 71%); m.p. 290-291° dec; mass spectrum (Cl, CH4) 282 (M+1); 1H-NMR (DMSO-d6)δ: 11.90 (br s, 1, NH), 8.03 (s, 1, H-8), 6.78 (br s, 2, NH2), 4.95-4.70 (m, overlapping d at 4.78, J=27 Hz, total 2, CHN and OH), 4.7-4.6 (m, 1, CH2OH), 4.1-4.0 (m, 1, CHOH), 3.6-3.4 (m, 2, CH2O), 2.4-2.2 (m, 1, CH), 2.2-1.9 (m, 3, methylene), 1.7-1.5 (m, 1, 1/2CH2); [α]20589 +6.43°, [α]20578 +6.71°, [α]20546 +7.43°, [α]20436 +8.43°, [α]20 365 +8.43° (c=0.70, 0.1N NaOH).

Provenance & Evidence