6-Amino-1-(cyclohexylmethyl)-3-propyl-5-nitrosouracil → HCID 178456488, compound

HRID 1955642Notes

Reaction equation

HRID 1955642 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][CH2:17][CH3:18])[C:4](=[O:19])[C:3]=1[N:20]=O.C1(CN2C(N)=C(N)C(=O)N(CCC)C2=O)CCCCC1.[CH:42]([C:44]1[CH:45]=[C:46]([CH:52]=[CH:53][CH:54]=1)[CH:47]=[CH:48][C:49]([OH:51])=[O:50])=O>>[CH:9]1([CH2:8][N:7]2[C:2]3[NH:1][C:42]([C:44]4[CH:45]=[C:46]([CH:52]=[CH:53][CH:54]=4)/[CH:47]=[CH:48]/[C:49]([OH:51])=[O:50])=[N:20][C:3]=3[C:4](=[O:19])[N:5]([CH2:16][CH2:17][CH3:18])[C:6]2=[O:15])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

4

Reactant 3

HCID 190713056-Amino-1-(cyclohexylmethyl)-3-propyl-5-nitrosouracilHCID 190713291-(Cyclohexylmethyl)-5,6-diamino-3-propyluracilHCID 542035293-Formylcinnamic acid

Product 1

HCID 178456488HCID 178456488, compoundYield 75%

Procedure

In the manner of step (d) of Example 1, 6amino-1-(cyclohexylmethyl)-3-propyl-5-nitrosouracil (step (c) example 12, 2.355 g, 8.00 mmol) was reduced to 1-(cyclohexylmethyl)-5,6-diamino-3-propyluracil, which was condensed with 3-formylcinnamic acid (T. Higa, A. J. Krubsack, J. Org. Chem. 1975, 40: 3037-3045, 1.424 g, 8.00 mmol) to give (E)-3-[3-(cyclohexylmethyl)-1,2,3,6-tetrahydro-2,6dioxo-1-propyl-9H-purin-8-yl]cinnamic acid as a pale yellow solid (2.632 g, 75%), m.p. >350° C.; 1H-NMR (DMSO-d6) consistent with structure.

Sources & evidence

ORD record
ord-1a7bf41247324bfbacfd710cb4f83da9
Source dataset
uspto-grants-1998_07
Patent number
US05776940

Reaction notes

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