Process for preparing 6-phenoxypyrimidin-4-ol derivatives in the presence of a quinuclidine or a n-methyl pyrrolidine derivatives

A process for preparing a compound of formula (I)

• which comprises either:
• a) reacting a compound of formula (II)
• with a compound of formula R6—OH, or a salt thereof, in the presence of between 0.05 and 40 mol % of
• (i) a quinuclidine-based molecule of formula (VI):
• (ii) the acid salt of the quinuclidine-based molecule of formula (VI);
• or
• (iii) an optionally 3-substituted N-methyl pyrrolidine of formula (VII):
• (iv) the acid salt of the optionally 3-substituted N-methyl pyrrolidine of formula (VII);
• or
• b) reacting a compound of formula (III)
• with a compound of formula (IV)
• or a salt thereof, in the presence of between 0.05 and 40 mol % of
• (i) a quinuclidine-based molecule of formula (VI):
• (ii) the acid salt of the quinuclidine-based molecule of formula (VI);
• or
• (iii) an optionally 3-substituted N-methyl pyrrolidine of formula (VII):
• (iv) the acid salt of the optionally 3-substituted N-methyl pyrrolidine of formula (VII);
• wherein:
• R1, R2, R3 and R4 are, independently, hydrogen, halogen, cyano, nitro, alkylcarbonyl, formyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, or optionally halogen-substituted alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl;
• R5 is hydrogen, halogen, cyano, nitro, alkylcarbonyl, formyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, or optionally halogen-substituted alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulponyl, or
• wherein * denotes the point of attachment to the phenyl radical of formula (I);
• R6 is substituted or unsubstituted aryl or heterocyclyl, or the salt thereof;
• R7 is hydrogen, fluorine, chlorine or bromine,
• R10, R11, R12, R13, R14 and R15 are, independently, hydrogen, fluorine, methyl, methoxy, methylene or cyano, or, independently, R10 and R11, R12 and R13, R14 and R15 together form ═O, ═S, ═N or ═CR30R31, wherein R30 and R31 are, independently, hydrogen or a substituent;
• R16, R17, R18, R19, R20 and R21 are, independently, hydrogen, fluorine, alkenyl, alkynyl, alkylcarbonyl, formyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkyl, aryl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl aryl groups, heterocyclyl, cycloalkyl, alkoxy, aryloxy, cycloalkyloxy, optionally substituted silyloxy, or, independently, R16 and R17, R18 and R19 and R20 and R21 together form ═O, ═S, ═N or ═CR30R31, wherein R30 and R31 are, independently, hydrogen or a substituent;
• R22 is hydrogen, fluorine, alkenyl, alkynyl, alkylcarbonyl, formyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkyl, aryl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl aryl groups, heterocyclyl, cycloalkyl, alkoxy, aryloxy, cycloalkyloxy or optionally substituted silyloxy;
• R23 is hydrogen or a C1-4 straight chain or branched alkyl;
• with the proviso that R6 and the radical:
• are different from each other.