Phthalaldehydic acid → 1,3-Bis(cyclohexylmethyl)-5,6-diaminouracil

HRID 2304835Notes

Reaction equation

HRID 2304835 reaction equation
NC1N(CC2CCCCC2)C(=O)N(CC2CCCCC2)C(=O)C=1.[NH2:24][C:25]1[N:30]([CH2:31][CH:32]2[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]2)[C:29](=[O:38])[N:28]([CH2:39][CH:40]2[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]2)[C:27](=[O:46])[C:26]=1[N:47]=O.[CH:49]([C:51]1[CH:59]=[CH:58][CH:57]=[CH:56][C:52]=1[C:53]([OH:55])=[O:54])=O>>[CH:32]1([CH2:31][N:30]2[C:25]([NH2:24])=[C:26]([NH2:47])[C:27](=[O:46])[N:28]([CH2:39][CH:40]3[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]3)[C:29]2=[O:38])[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]1.[CH:40]1([CH2:39][N:28]2[C:27](=[O:46])[C:26]3[N:47]=[C:49]([C:51]4[CH:59]=[CH:58][CH:57]=[CH:56][C:52]=4[C:53]([OH:55])=[O:54])[NH:24][C:25]=3[N:30]([CH2:31][CH:32]3[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]3)[C:29]2=[O:38])[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]1

Participants

5

Reactant 3

HCID 8406Phthalaldehydic acidHCID 222449706-Amino 1,3-bis(cyclohexylmethyl)-5-nitrosouracilHCID 222449716-Amino-1,3-bis(cyclohexylmethyl)uracil

Product 2

HCID 222449751,3-Bis(cyclohexylmethyl)-5,6-diaminouracilHCID 178524287HCID 178524287, compound

Procedure

1,3-Bis(cyclohexylmethyl)-5,6-diaminouracil was prepared as in part (d) of Example 1 by reduction of 1, 6-amino 1,3-bis(cyclohexylmethyl)-5-nitrosouracil (2.00 g) and immediately condensed with 2-formylbenzoic acid (Aldrich, 1.424 g) by the method of J. Perumattam (Synthetic Commun. 1989, 19: 3367-3370) to give title compound as an off-white solid off-white solid (1.22 g, 46%), m.p. 271-274° C.; 1H-NMR (DMSO-d6) consistent with structure.

Sources & evidence

ORD record
ord-f387342b117246b69a26522210616ef2
Source dataset
uspto-grants-2002_08
Patent number
US06437124B1

Reaction notes

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