Formaldehyde → Octanoic acid{5-[(dibenzylamino)-methyl]-4-oxo-4,7-dihydro-3h-pyrrolo[2,3-d]pyrimidin-2-yl}-amide

HRID 412742Notes

Reaction equation

[O:1]=[C:2]1[NH:7][C:6]([NH:8][C:9](=[O:17])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[N:5][C:4]2[NH:18][CH:19]=[CH:20][C:3]1=2.[NH:21]([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[CH2:36]=O>>[CH2:29]([N:21]([CH2:36][C:20]1[C:3]2[C:2](=[O:1])[NH:7][C:6]([NH:8][C:9](=[O:17])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[N:5][C:4]=2[NH:18][CH:19]=1)[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

Reactant 3

HCID 712Formaldehyde

HCID 7656Dibenzylamine

HCID 136050864N-(4-Oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-2-yl)octanamide

Product 1

HCID 135754624Octanoic acid{5-[(dibenzylamino)-methyl]-4-oxo-4,7-dihydro-3h-pyrrolo[2,3-d]pyrimidin-2-yl}-amide

Procedure

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.

Sources & evidence

ORD record: ord-25bcdb2861354a5a8f5aaa8d74b251d9
Source dataset: uspto-grants-2003_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06562969B1

Reaction notes

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