Ethyl Acetoacetate → HCID 12229214, compound

HRID 262507Notes

Reaction equation

[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[O-]CC.[Na+].Cl[CH2:15][C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1>>[N:18]1[CH:19]=[CH:20][CH:21]=[C:16]([CH2:15][CH:2]([C:3]([CH3:5])=[O:4])[C:1]([O:7][CH2:8][CH3:9])=[O:6])[CH:17]=1

Participants

Reactant 3

HCID 8868Ethyl Acetoacetate

HCID 183583-(Chloromethyl)pyridine

HCID 2723922Sodium ethoxide

Product 1

HCID 12229214HCID 12229214, compound

Procedure

Reaction of ethyl acetoacetate with sodium ethoxide and 3-(chloromethyl)pyridine gives ethyl α-(3-pyridylmethyl)acetoacetate which gives 5-(3-pyridylmethyl)-6-methyl-2-thiouracil m.p. 332°-335° when treated with thiourea and sodium ethoxide. Substitution of 5-(3-pyridylmethyl)-6-methyl-2-thiouracil for 5-(4-pyridylmethyl)-2-thiouracil in the general procedure of Example 1 gives 2-[2-(5-methyl-4-imidazolylmethylthio)ethylamino]-5-(3-pyridylmethyl)-6-methyl-4-pyrimidone, m.p. 128°-131°. 5-(3-Pyridylmethyl)-6-methyl-2-methylthio-4-pyrimidone and m.p. 208°-211°.

Sources & evidence

ORD record: ord-d8a0da5183d54704937c432c847a4008
Source dataset: uspto-grants-1979_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04154834

Reaction notes

Loading…