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Synthesis of methotrexate-3-15N-2-15NH2. A convenient method for preparation of guanidiine-15N3

✍ Scribed by Joseph I. Degraw; Kenneth J. Ryan; William T. Colwell; John R. P. Arnold; Gordon C. K. Roberts

Publisher: John Wiley and Sons
Year: 1988
Tongue: French
Weight: 205 KB
Volume: 25
Category: Article
ISSN: 0022-2135
DOI: 10.1002/jlcr.2580251103

No coin nor oath required. For personal study only.

✦ Synopsis

Condensation of guanidine-15N3 with 4-[ N( 2-amino-3-cyano-5-pyrazinylmethyl)-N-methylamino] benzoic acid (1) in refluxing methanol afforded 4amino-4-deoxy-N10-methylpteroic-3-15N-2-15NH2 (2). indicated no label introduction at the pterin N1 position. Coupling of 2. with diethyl L-gluatmate and subsequent alkaline hydrolysis yielded methotrexate-3-15N-2-15NH2 (3). Triply 15N-labeled guanidine was readily prepared from thiocyanic-15N acid (derived from KSC15N) and au~monia-~~N by heating the resultant ammonium t h i o ~y a n a t e -~~N ~ at 180°C, followed by isolation as the water insoluble picrate salt.

The mass spectrum clearly

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