Ethyl formate → HCID 12783848, compound

HRID 637743Notes

Reaction equation

[CH3:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([O:12]CC)=O)=[CH:4][CH:3]=1.[Na].[CH:16](OCC)=O.[NH2:21][C:22]([NH2:24])=[S:23]>>[CH3:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][C:9]2[C:10](=[O:12])[NH:21][C:22](=[S:23])[NH:24][CH:16]=2)=[CH:4][CH:3]=1

Participants

Reactant 4

HCID 8025Ethyl formate

HCID 2723790Thiourea

HCID 3018102Ethyl 3-(6-methyl-3-pyridyl)propionate

HCID 5360545Sodium

Product 1

HCID 12783848HCID 12783848, compound

Procedure

3-(6-Methyl-3-pyridyl)propenoic acid, m.p. 213.5-215.5°, was prepared by reacting 6-methylpyridine-3-carboxaldehyde with malonic acid in pyridine with piperidine catalyst, and was converted into the corresponding ethyl ester m.p. 36°-37° which was reduced with hydrogen and palladium-on-charcoal catalyst to give ethyl 3-(6-methyl-3-pyridyl)-propionate (oil). This ester was reacted with sodium and ethyl formate and the product treated with thiourea to give 5-(6-methyl-3-pyridylmethyl)-2-thiouracil m.p. 240°-241° which was alkylated with methyl iodide in the presence of sodium hydroxide at 70° to give 5-(6-methyl-3-pyridylmethyl)-2-methylthio-4-pyrimidone, m.p. 197°-198.5°.

Sources & evidence

ORD record: ord-6190d7b53bcf47a882d9b9e1ee4682c8
Source dataset: uspto-grants-1985_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04558128

Reaction notes

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