Sodium Hydroxide → HCID 15666911, compound

Participants

Reaction Steps

A solution of 4 (190 mg, 0.521 mmol) in Me2SO (17 mL) was treated with 1 N NaOH (0.75 mL). After 20 hours at 20°-23° C., the solution was found by TLC (CHCl3 -MeOH, 4:1) examination to contain a small amount of unchanged 4. More 1N NaOH (0.50 mL) was added to the solution, kept at 20°-23° C., and 2 hours later TLC showed completed disappearance of 4. The Me2SO was then removed by distillation in vacuo (less than 1 mm, bath to 45° C). The residue was dissolved in H2O (3 mL), and the resulting clear solution was carefully treated dropwise with 1N HCl to produce pH 5 and cause precipitation of 5 as a pale-beige solid. The mixture was chilled in a refrigerator for several hours before the solid was collected and dried; yield 165 mg (82%). Anal. Calcd. for C19H21N5O2.2H2O: C, 58.90; H, 6.50; N, 18.08. Found: C, 59.40; H, 6.14; N, 17.63. Spectral data: mass, m/z 352, MH+ for C19H21N5O2 ; UV λmax 234 nm (ε 39 300), 322 (7730) at pH 1; 235 nm (ε 37 800), 335 (6050) at pH 7; 236 nm (ε 37 600), 346 (6730) at pH 13.

Provenance & Evidence