Thiourea → HCID 23349180, compound

HRID 1855865Notes

Reaction equation

HRID 1855865 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH:8]([C:14]([CH3:16])=O)[C:9](OCC)=[O:10])[CH:2]=1.[NH2:17][C:18]([NH2:20])=[S:19].[O-]CC.[Na+]>C(O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][C:8]2[C:9](=[O:10])[NH:17][C:18](=[S:19])[NH:20][C:14]=2[CH3:16])[CH:2]=1

Participants

5

Reactant 3

HCID 2723790ThioureaHCID 2723922Sodium ethoxideHCID 12229214HCID 12229214, compound

Product 1

HCID 23349180HCID 23349180, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of pyridine-3-carboxaldehyde (48 g), ethyl acetoacetate (52 g) aqueous piperidine acetate (40% 4.8 g) and 5% palladium on charcoal catalyst (50% wet, 2.48 g) was hydrogenated at 100 p.s.i. at 30° for 22 hours. The mixture was diluted with ether, filtered and the filtrate was evaporated and distilled under reduced pressure to give ethyl α-(3-pyridylmethyl)acetoacetate (b.p. 146°/1 mmHg). This ester was refluxed with thiourea and sodium ethoxide in ethanol, and the mixture was subsequently acidified to give 5-(3-pyridylmethyl)-6-methyl-2-thiouracil m.p. 328°-331°.

Sources & evidence

ORD record
ord-ac49cf18501841ec84dba000ee495b30
Source dataset
uspto-grants-1980_08
Patent number
US04216318

Reaction notes

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