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

HRID 891246Notes

Reaction equation

HRID 891246 reaction equation
[CH:1]1([CH2:7][N:8]2[C:16](=[O:17])[C:15]3[N:14]=[C:13](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.NC1N(CC2CCCCC2)C(=O)N(CC2CCCCC2)C(=O)C=1N=O.C([C:64]1[CH:72]=[CH:71][C:67]([C:68]([OH:70])=[O:69])=[CH:66][CH:65]=1)=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:1]1([CH2:7][N:8]2[C:16](=[O:17])[C:15]3[N:14]=[C:13]([C:66]4[CH:65]=[CH:64][CH:72]=[CH:71][C:67]=4[C:68]([OH:70])=[O:69])[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])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 120884-Formylbenzoic 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 (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-c3061fe80d3e40fca22e72ad628b209a
Source dataset
uspto-grants-2006_02
Patent number
US07002012B2

Reaction notes

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