Octanoyl chloride → Octanoic acid(7-octanoyl-4-oxo-4,7-dihydro-3h-pyrrolo[2,3-d]pyrimidin-2-yl)-amide

Participants

Reaction Steps

The syntheses of 4-[(2-amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-5-ylmethyl)-amino]-benzoic acid 21 and 2-amino-5-{[4-(4-amino-benzyl)-phenylamino]-methyl}-3,7-dihydro-pyrrolo[2,3-d]pyrimidin-4-one 24 are shown in FIG. 22. FIG. 22A details the synthesis of 4-[(2-amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-5-ylmethyl)-amino]-benzoic acid 21. 2-amino-3,7-dihydro-pyrrolo[2,3-d]pyrimidin-4-one 15 is reacted with octanoyl chloride in pyridine to produce octanoic acid(7-octanoyl-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-2-yl)-amide 16, which is then treated with ammonia in methanol to produce octanoic acid(4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-2-yl)-amide 17. Octanoic acid(4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-2-yl)-amide 17 is reacted with (PhCH2)2NH in formaldehyde to produce octanoic acid{5-[(dibenzylamino)-methyl]-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-2-yl}-amide 18. Octanoic acid{5-[(dibenzylamino)-methyl]-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-2-yl}-amide 18 is reacted with 4-amino-methylbenzoate 19 to yield 4-[(2-octanoylamino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-5-ylmethyl)-amino]-benzoic acid methyl ester 20. Treatment of 4-[(2-octanoylamino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-5-ylmethyl)-amino]-benzoic acid methyl ester 20 with 5 M KOH in ethanol yields 4-[(2-amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-5-ylmethyl)-amino]-benzoic acid 21.

Provenance & Evidence