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

HRID 891247Notes

Reaction equation

HRID 891247 reaction equation
[CH:1]1([CH2:7][N:8]2[C:16](=[O:17])[C:15]3[N:14]=C(C4C=CC(/C=C/C(O)=O)=CC=4)[NH:12][C:11]=3[N:10]([CH2:29][CH:30]3[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]3)[C:9]2=[O:36])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:37][C:38]1[N:43]([CH2:44][CH:45]2[CH2:50][CH2:49][CH2:48][CH2:47][CH2:46]2)[C:42](=[O:51])[N:41]([CH2:52][CH:53]2[CH2:58][CH2:57][CH2:56][CH2:55][CH2:54]2)[C:40](=[O:59])[C:39]=1[N:60]=O.[CH:62]([C:64]1[CH:72]=[CH:71][CH:70]=[CH:69][C:65]=1[C:66]([OH:68])=[O:67])=O>>[CH:30]1([CH2:29][N:10]2[C:11]([NH2:12])=[C:15]([NH2:14])[C:16](=[O:17])[N:8]([CH2:7][CH:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)[C:9]2=[O:36])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]1.[CH:53]1([CH2:52][N:41]2[C:40](=[O:59])[C:39]3[N:60]=[C:62]([C:64]4[CH:72]=[CH:71][CH:70]=[CH:69][C:65]=4[C:66]([OH:68])=[O:67])[NH:37][C:38]=3[N:43]([CH2:44][CH:45]3[CH2:50][CH2:49][CH2:48][CH2:47][CH2:46]3)[C:42]2=[O:51])[CH2:58][CH2:57][CH2:56][CH2:55][CH2:54]1

Participants

5

Reactant 3

HCID 8406Phthalaldehydic acidHCID 222449706-Amino 1,3-bis(cyclohexylmethyl)-5-nitrosouracilHCID 178525288HCID 178525288, compound

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-0ab4837efb1147698b9f1d5f0857df3e
Source dataset
uspto-grants-2006_02
Patent number
US07002012B2

Reaction notes

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