Uracil → 2-Methylthio-5-(3-pyridyl)methoxy-4-pyrimidone

HRID 358480Notes

Reaction equation

HRID 358480 reaction equation
[Na].[CH:2](OCC)=O.N1C=CC=C(COCC(OCC)=O)C=1.C(C(OCC1C=NC=CC=1)C(OCC)=O)=O.NC(N)=S.[N:41]1[CH:46]=[CH:45][CH:44]=[C:43]([CH2:47][O:48][C:49]2[C:50](=[O:56])[NH:51][C:52](=[S:55])[NH:53][CH:54]=2)[CH:42]=1.N1C=CC(=O)NC1=O.[OH-].[Na+].CI>CCOCC.O.C(O)C>[CH3:2][S:55][C:52]1[NH:51][C:50](=[O:56])[C:49]([O:48][CH2:47][C:43]2[CH:42]=[N:41][CH:46]=[CH:45][CH:44]=2)=[CH:54][N:53]=1

Participants

13

Reactant 9

HCID 1174UracilHCID 6328Methyl iodideHCID 8025Ethyl formateHCID 14798Sodium HydroxideHCID 2723790ThioureaHCID 5360545Sodium2×HCID 13373523Ethyl formyl-(3-pyridylmethoxy)acetateHCID 133735255-(3-Pyridylmethoxy)-2-thiouracilHCID 19261392Ethyl 2-((pyridin-3-yl)methoxy)acetate

Product 1

HCID 133735192-Methylthio-5-(3-pyridyl)methoxy-4-pyrimidone

Reagents, catalysts & solvents 3

HCID 702EthanolSolvent2×HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

Following the above procedure, 3.03 g. of sodium were suspended in anhydrous ether in a nitrogen atmosphere. 5.93 g. of ethyl formate plus 14.1 g. of ethyl 3-pyridylmethoxyacetate were added. The product of the reaction, ethyl formyl-(3-pyridylmethoxy)acetate as the sodium salt, was suspended in 175 ml. of ethanol and 5.8 g. of thiourea were added. The product of this reaction, 5-(3-pyridylmethoxy)-2-thiouracil, melted at 243°-245° C.; weight=10.4 g. 9.9 g. of the uracil were slurried in 80 ml. of ethanol. A solution containing 1.78 g. of sodium hydroxide and 38 ml. of water was added followed by 4.86 g. of methyl iodide. 1.46 g. of 2-methylthio-5-(3-pyridyl)methoxy-4-pyrimidone were obtained melting at 186°-187° C.

Workup

  1. additionA solution containing 1.78 g

Sources & evidence

ORD record
ord-108a0dafa582444e931abbd051fb790a
Source dataset
uspto-grants-1984_08
Patent number
US04468399

Reaction notes

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