2-Methylpropylenediamine → HCID 178457531, compound

Participants

Reaction Steps

2-Amino-6-chloro-4-hydroxy-5-nitropyrimidine, 1.94 g, was finely powdered and dissolved in approximately 200 ml boiling absolute ethanol and filtered while hot to remove the insoluble 2-amino-4,6-dihydroxy-5-nitropyrimidine (sole contaminant), leaving a solution containing 9.0 mmoles of (IIa). This was taken again to reflux and 0.88 g (20 mmoles) 1,2-diamino-2-methylpropane (99% pure) added all at once with stirring. The progress of the reaction was monitored on Partisil SCX (25×0.46 cm) eluted with 0.1M ammonium hydroxide made to pH 3.3 with formic acid/methanol, 9:1, by absorbance at 254 and 330 nm. After 2 hrs stirring at reflux, greater than 99% of (IIa) had been consumed and the majority of product had fallen out of solution. After being kept at -15° C. overnight in order to complete this precipitation, the reaction filtered, washed with a few ml cold absolute ethanol and 40 ml ether, and vacuum dried over P2O5, gave 2.43 g of the monohydrochloride salt (97% yield): UV (0.1N HCl) εmax 331 nm, 285-290 nm sh, 233 nm sh; 1H-NMR (DMSO-D6) δ1.13 (6H, s, C(CH3)2), δ3.50 (2H, d, J=5Hz, --N--CH2 (singlet if D2O added). Greater than 99% of the UV330 and 98% of the UV254 absorbance in a chromatogram of this material resides in a single well-shaped peak. No evidence for the presence of any 2-amino-6-(2-amino-1,1-dimethylethylamino)-4-hydroxy-5-nitropyrimidine can be seen by ether HPLC or NMR.

Provenance & Evidence