Pyrimidine compound

A process for preparing a compound of formula (1):

• comprising:
• Step 1) reacting the compound of the formula (6):
• wherein Q1 is —Y1′—CHO, Y1′ is absent or alkylene, and —Y1′—(CR9R10)— is —Y1—, with a compound of the following formula:
• wherein R8 is hydrogen or an amino protecting group, in the presence of a reducing agent to obtain a compound of formula (2):
• and
• Step 2) if R8 is an amino protecting group, removing the amino protecting group of R8, and reacting the compound of formula (2) with a compound of the formula (3):
• in the presence of a condensing agent;
• wherein:
• X is methylene, oxygen, sulfur, SO, SO2 or NR7 wherein R7 is hydrogen or an alkyl group of 1 to 3 carbon atoms;
• R1 and R2 are independently hydrogen or a substituted or unsubstituted alkyl group of 1 to 6 carbon atoms, provided that when the alkyl group is substituted, it is substituted with 1 to 4 substituents independently selected from the group consisting of hydroxy, halogen and an alkoxy group of 1 to 6 carbon atoms;
• R3 is an alkyl group of 1 to 6 carbon atoms, an alkoxy group of 1 to 6 carbon atoms, or an alkylthio group of 1 to 6 carbon atoms;
• R4 is hydrogen, halogen, hydroxy, an alkyl group of 1 to 6 carbon atoms, an alkoxy group of 1 to 6 carbon atoms, or cyano;
• Y1 is —(CR9R10)p—, —CH═CH—(CR9R10)q—, or —C≡C—(CR9R10)q′— wherein R9 and R10 are each independently hydrogen or an alkyl group of 1 to 4 carbon atoms;
• Y2 is a single bond;
• L is a substituted or unsubstituted straight chain alkylene of 2 to 6 carbon atoms, wherein any one of the methylene groups in the straight chain alkylene of L is optionally replaced with carbonyl group, and provided that when the straight chain alkylene is substituted, it is substituted with 1 to 4 substituents independently selected from the group consisting of an alkyl group of 1 to 5 carbon atoms, hydroxy and halogen,
• or L is a divalent 4- to 8-membered cycloalkane, provided that when the cycloalkane is substituted, it is substituted with 1 to 4 substituents selected from the group consisting of an alkyl group of 1 to 5 carbon atoms, hydroxy, and halogen;
• R5 and R6 are each independently hydrogen or a substituted or unsubstituted alkyl group of 1 to 6 carbon atoms, provided that when the alkyl group is substituted, it is substituted with 1 to 4 substituents independently selected from the group consisting of hydroxy and halogen;
• or R5 or R6 is bonded to any carbon atom of L to form a 4- to 8-membered nitrogen-containing saturated heterocycle, provided that when the 4- to 8-membered nitrogen-containing saturated heterocycle is substituted, it is substituted with 1 to 4 substituents independently selected from the group consisting of methyl, ethyl, propyl, hydroxymethyl, hydroxyethyl, carbonyl, hydroxy, and halogen;
• or R5 and R6 are taken together to form a substituted or unsubstituted 5- to 8-membered nitrogen-containing saturated heterocycle, provided that when the 5- to 8-membered nitrogen-containing saturated heterocycle is substituted, it is substituted with 1 to 4 substituents independently selected from the group consisting of methyl, ethyl, propyl, hydroxymethyl, hydroxyethyl, carbonyl, hydroxy, and halogen;
• m is 0 or 1;
• p is an integer of 1 to 6;
• q and q′ are each independently an integer of 0 to 4;
• r is an integer of 0 to 5, and r′ is an integer of 1 to 5, provided that r′ is an integer of 2 or more when the sum of r and r′ is 5 or less and Y2 is a single bond;
• and
• each is independently a single bond or a double bond.

A process for preparing a compound of formula (1):

• comprising:
• Step 1) reacting the compound of the formula (4):
• with a compound of the following formula:
• wherein R8 is hydrogen or an amino protecting group, in the presence of a condensing agent to obtain a compound of formula (2):
• and
• Step 2) if R8 is an amino protecting group, removing the amino protecting group of R8, and reacting the compound of formula (2) with a compound of the formula (3):
• in the presence of a condensing agent;
• wherein:
• X is methylene, oxygen, sulfur, SO, SO2 or NR7 wherein R7 is hydrogen or an alkyl group of 1 to 3 carbon atoms;
• R1 and R2 are independently hydrogen or a substituted or unsubstituted alkyl group of 1 to 6 carbon atoms, provided that when the alkyl group is substituted, it is substituted with 1 to 4 substituents independently selected from the group consisting of hydroxy, halogen and an alkoxy group of 1 to 6 carbon atoms;
• R3 is an alkyl group of 1 to 6 carbon atoms, an alkoxy group of 1 to 6 carbon atoms, or an alkylthio group of 1 to 6 carbon atoms;
• R4 is hydrogen, halogen, hydroxy, an alkyl group of 1 to 6 carbon atoms, an alkoxy group of 1 to 6 carbon atoms, or cyano;
• Y1 is a single bond, —(CR9R10)p—, —CH═CH—(CR9R10)q—, —C≡C—(CR9R10)q′— or —(CR9R10)r—O—(CR9′R10′)r′— wherein R9, R10, R9′ and R10′ are independently hydrogen or an alkyl group of 1 to 4 carbon atoms;
• Y2 is —C(O)—;
• L is a substituted or unsubstituted straight chain alkylene of 2 to 6 carbon atoms, wherein any one of the methylene groups in the straight chain alkylene of L is optionally replaced with carbonyl group, and provided that when the straight chain alkylene is substituted, it is substituted with 1 to 4 substituents independently selected from the group consisting of an alkyl group of 1 to 5 carbon atoms, hydroxy and halogen,
• or L is a divalent 4- to 8-membered cycloalkane, provided that when the cycloalkane is substituted, it is substituted with 1 to 4 substituents selected from the group consisting of an alkyl group of 1 to 5 carbon atoms, hydroxy, and halogen;
• R5 and R6 are each independently hydrogen or a substituted or unsubstituted alkyl group of 1 to 6 carbon atoms, provided that when the alkyl group is substituted, it is substituted with 1 to 4 substituents independently selected from the group consisting of hydroxy and halogen;
• or R5 or R6 is bonded to any carbon atom of L to form a 4- to 8-membered nitrogen-containing saturated heterocycle, provided that when the 4- to 8-membered nitrogen-containing saturated heterocycle is substituted, it is substituted with 1 to 4 substituents independently selected from the group consisting of methyl, ethyl, propyl, hydroxymethyl, hydroxyethyl, carbonyl, hydroxy, and halogen;
• or R5 and R6 are taken together to form a substituted or unsubstituted 5- to 8-membered nitrogen-containing saturated heterocycle, provided that when the 5- to 8-membered nitrogen-containing saturated heterocycle is substituted, it is substituted with 1 to 4 substituents independently selected from the group consisting of methyl, ethyl, propyl, hydroxymethyl, hydroxyethyl, carbonyl, hydroxy, and halogen;
• m is 0 or 1;
• p is an integer of 1 to 6;
• q and q′ are each independently an integer of 0 to 4;
• r is an integer of 0 to 5, and r′ is an integer of 1 to 5;
• and
• each is independently a single bond or a double bond.