US 12,723,032 B2Granted

Method for producing uracil compound

AssigneeNippon Soda Co., Ltd.

InventorsTakuma Ishihara, Shinya Koubori, Takaaki Teranishi

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Abstract

An object of the present invention is to provide an industrially advantageous method for producing uracil compound, which is a production intermediate of a 2,6-dioxo-3,6-dihydropyrimidine compound, and ureidomethylene compound applicable as a raw material for uracil compounds. The present invention is characterized in that uracil compound, which is a production intermediate of a 2,6-dioxo-3,6-dihydropyrimidine compound, is produced by subjecting a compound of formula (II) below or a salt thereof to chemical reaction in the presence of an organic base or an inorganic base. In formula (II), X1 represents a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group, X2 represents a hydrogen atom or a substituted or unsubstituted linear C1-6 alkyl group, etc., R1 represents a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group, etc., R2 represents a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group, and R3 represents a substituted or unsubstituted C1-6 alkyl group, etc.

Claims4

Dependent claims

A method for producing a compound of formula (I) or a salt thereof:

wherein in formula (I),
the crossed double bond symbol represents a cis or trans double bond configuration or mixtures thereof;
X1 represents a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group;
R1 represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5 to 6-membered ring heterocyclyl group;
R2 represents a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group;
X2 represents a hydrogen atom, a substituted or unsubstituted linear C1-6 alkyl group, a substituted or unsubstituted linear C2-6 alkenyl group, a substituted or unsubstituted linear C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, a substituted or unsubstituted 4 to 6-membered ring heterocyclyl group, a group represented by RNRNN—, a group represented by RN—CO—NRN—, a group represented by RN—CO—CO—NRN—, a group represented by RN—O—CO—NRN—, a group represented by RNRNN—CO—NRN, a group represented by RNRNN—CO—CO—NRe—, a group represented by RN, CS—NRN—, a group represented by RNRNN—CS—NRN—, a group represented by RNSO2—NRN—, or a group represented by RN—C(═NRN)—NRN—;
each RN independently represents a hydrogen atom, a substituted or unsubstituted linear C1-6 alkyl group, a substituted or unsubstituted linear C2-6 alkenyl group, a substituted or unsubstituted linear C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 4 to 6-membered ring heterocyclyl group, where RN and RN can together form a divalent organic group, the method comprising:
subjecting a compound of formula (II) or a salt thereof to chemical reaction in the presence of an organic base or an inorganic base:
wherein in formula (II),
the crossed double bond symbol represents a cis or trans double bond configuration or mixtures thereof,
R1, R2, X1, and X2 represent the same meaning as those in formula (I)
R3 represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, or a substituted or unsubstituted C6-10 aryl group.

9 more elements

A compound of formula (II) or a salt thereof:

wherein in formula (II),
the crossed double bond symbol represents a cis or trans double bond configuration or mixtures thereof;
X1 represents a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group;
R1 represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5 to 6-membered ring heterocyclyl group;
R2 represents a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group;
X2 represents a hydrogen atom, a substituted or unsubstituted linear C1-6 alkyl group, a substituted or unsubstituted linear C2-6 alkenyl group, a substituted or unsubstituted linear C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, a substituted or unsubstituted 4 to 6-membered ring heterocyclyl group, a group represented by RNRNN—, a group represented by RN—CO—NRN—, a group represented by RN—CO—CO—NRN, a group represented by RN—O—CO—NRN—, a group represented by RNRNN—CO—NRN, a group represented by RNRNN—CO—CO—NRe—, a group represented by RN—CS—NRN—, a group represented by RNRNN—CS—NRN—, a group represented by RNSO2—NRN—, or a group represented by RN—C(═NRN)—NRN—;
each RN independently represents a hydrogen atom, a substituted or unsubstituted linear C1-6 alkyl group, a substituted or unsubstituted linear C2-6 alkenyl group, a substituted or unsubstituted linear C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 4 to 6-membered ring heterocyclyl group, where RN and RN can together form a divalent organic group;
and
R3 represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, or a substituted or unsubstituted C6-10 aryl group.

6 more elements

Dependencies are inferred from the claim text.