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

HRID 2304834Notes

Reaction equation

HRID 2304834 reaction equation
[NH2:1][C:2]1[N:7]([CH2:8][CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[C:6](=[O:15])[N:5]([CH2:16][CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[C:4](=[O:23])[CH:3]=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.C([C:51]1[CH:59]=[CH:58][C:54]([C:55]([OH:57])=[O:56])=[CH:53][CH:52]=1)=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:17]1([CH2:16][N:5]2[C:4](=[O:23])[C:3]3[N:24]=[C:25]([C:53]4[CH:52]=[CH:51][CH:59]=[CH:58][C:54]=4[C:55]([OH:57])=[O:56])[NH:1][C:2]=3[N:7]([CH2:8][CH:9]3[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]3)[C:6]2=[O:15])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]1

Participants

5

Reactant 3

HCID 120884-Formylbenzoic 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 (1.00 g) and immediately condensed with 4-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 an off-white solid (720 mg, 54%), m.p. >300° C.; 1H-NMR (DMSO-d6) consistent with structure.

Sources & evidence

ORD record
ord-ed453a0a49334e68805105d0e3bf88de
Source dataset
uspto-grants-2002_08
Patent number
US06437124B1

Reaction notes

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