Potassium Hydroxide → 2-Amino-5-{[4-(4-amino-benzyl)-phenylamino]-methyl}-3,7-dihydro-pyrrolo[2,3-d]pyrimidin-4-one

HRID 412744

Reaction equation

HRID 412744 reaction equation
[NH2:1][C:2]1[CH:36]=[CH:35][C:5]([CH2:6][C:7]2[CH:12]=[CH:11][C:10]([NH:13][CH2:14][C:15]3[C:23]4[C:22](=[O:24])[NH:21][C:20]([NH:25]C(=O)CCCCCCC)=[N:19][C:18]=4[NH:17][CH:16]=3)=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[OH-].[K+]>>[NH2:25][C:20]1[NH:21][C:22](=[O:24])[C:23]2[C:15]([CH2:14][NH:13][C:10]3[CH:9]=[CH:8][C:7]([CH2:6][C:5]4[CH:35]=[CH:36][C:2]([NH2:1])=[CH:3][CH:4]=4)=[CH:12][CH:11]=3)=[CH:16][NH:17][C:18]=2[N:19]=1

Participants

3

Reactant 2

HCID 14797Potassium HydroxideHCID 136050866octanoic acid (5-{[4-(4-amino-benzyl)-phenylamino]-methyl}-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-2-yl)-amide

Product 1

HCID 1360508672-Amino-5-{[4-(4-amino-benzyl)-phenylamino]-methyl}-3,7-dihydro-pyrrolo[2,3-d]pyrimidin-4-one

Procedure

The synthesis of 2-amino-5-{[4-(4-amino-benzyl)-phenylamino]-methyl}-3,7-dihydro-pyrrolo[2,3-d]pyrimidin-4-one 24 follows the same steps as the synthesis of 4-[(2-amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-5-ylmethyl)-amino]-benzoic acid 21, except that octanoic acid{5-[(dibenzylamino)-methyl]-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-2-yl}-amide 18 is reacted with 4,4′-methylene dianiline 22 to form octanoic acid (5-{[4-(4-amino-benzyl)-phenylamino]-methyl}-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-2-yl)-amide 23. Octanoic acid (5-{[4-(4-amino-benzyl)-phenylamino]-methyl}-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-2-yl)-amide 23 is then reacted with 5M KOH to form 2-amino-5-{[4-(4-amino-benzyl)-phenylamino]-methyl}-3,7-dihydro-pyrrolo[2,3-d]pyrimidin-4-one 24.

Sources & evidence

ORD record
ord-d70a0c662aa7405a9ccd9954d98bf4be
Source dataset
uspto-grants-2003_05
Patent number
US06562969B1

Linked notes

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