6-Amino 1,3-bis(cyclohexylmethyl)-5-nitrosouracil → HCID 178525309, compound

HRID 276806Notes

Reaction equation

HRID 276806 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])[C:3]=1[N:24]=O.C1(CN2C(N)=C(N)C(=O)N(CC3CCCCC3)C2=O)CCCCC1.[CH:50]([C:52]1[CH:53]=[C:54]([CH:60]=[CH:61][CH:62]=1)[CH:55]=[CH:56][C:57]([OH:59])=[O:58])=O>>[CH:17]1([CH2:16][N:5]2[C:4](=[O:23])[C:3]3[N:24]=[C:50]([C:52]4[CH:53]=[C:54]([CH:60]=[CH:61][CH:62]=4)/[CH:55]=[CH:56]/[C:57]([OH:59])=[O:58])[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])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

4

Reactant 3

HCID 222449706-Amino 1,3-bis(cyclohexylmethyl)-5-nitrosouracilHCID 222449751,3-Bis(cyclohexylmethyl)-5,6-diaminouracilHCID 542035293-Formylcinnamic acid

Product 1

HCID 178525309HCID 178525309, compoundYield 49%

Procedure

As in part (d) of Example, 1, 6-amino 1,3-bis(cyclohexylmethyl)-5-nitrosouracil (from step (c) example 1, 2.79 g, 8.00 mmol) was reduced to 1,3-bis(cyclohexylmethyl)-5,6-diaminouracil, and condensed with 3-formylcinnamic acid (T. Higa, A. J. Krubsack, J. Org. Chem. 1975, 40: 3037-3045, 1.424 g) to give (E)-3-[1,3-bis(cyclohexylmethyl)-1,2,3,6-tetrahydro-2,6-dioxo-9H-purin-8-yl]cinnamic acid as an off-white solid (1.947 g, 49%), m.p. >350° C.; 1H-NMR (DMSO-d6) consistent with structure.

Sources & evidence

ORD record
ord-f416425fa27646f7b0320219c3ecb030
Source dataset
uspto-grants-2002_03
Patent number
US06355646B1

Reaction notes

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