Patent ID: 8569494

Claim:
A method of preparing a compound of formula (I), the method comprising contacting a compound of formula (III) with R 1 —Y in a solvent, in the presence of dichloro[1,1′-bis(ditert-butylphosphino)ferrocene]palladium or dichlorobis(p-dimethylamino phenylditbutylphosphine)palladium(II), wherein said contacting occurs under conditions suitable to provide a compound of formula (I), wherein: X is halogen, B(OR + ) 2 or Sn(R ++ ) 3 ; Y is halogen, triflate, B(OR + ) 2 or Sn(R ++ ) 3 ; wherein a) when X is halogen, then Y is B(OR + ) 2 or Sn(R ++ ) 3 ; or b) when Y is halogen or triflate, then X is B(OR + ) 2 or Sn(R ++ ) 3 ; wherein each R + is independently hydrogen or substituted or unsubstituted C 1-3 alkyl, or each R + , together with the boron atom and the atoms to which they are attached, form a cyclic boronate; and R ++ is a C 1-4 alkyl; and wherein R 1 is substituted or unsubstituted C 1-8 alkyl, substituted or unsubstituted aryl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocyclyl, or substituted or unsubstituted heterocyclylalkyl; R 2 is H, substituted or unsubstituted C 1-8 alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted heterocyclylalkyl, substituted or unsubstituted aralkyl, or substituted or unsubstituted cycloalkylalkyl; R 3 and R 4 are each independently H, substituted or unsubstituted C 1-8 alkyl, substituted or unsubstituted aryl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted heterocyclylalkyl, substituted or unsubstituted aralkyl, substituted or unsubstituted cycloalkylalkyl, or R 3 and R 4 , together with the atom to which they are attached, form a substituted or unsubstituted cycloalkyl or substituted or unsubstituted heterocyclyl; or R 2 and one of R 3 and R 4 , together with the atoms to which they are attached, form a substituted or unsubstituted heterocyclyl; provided the compound is not 6-(4-hydroxyphenyl)-4-(3-methoxybenzyl)-3,4-dihydropyrazino[2,3-b]pyrazin-2(1H)-one, 6-(4-(1H-1,2,4-triazol-5-yl)phenyl)-3-(cyclohexylmethyl)-3,4-dihydropyrazino[2,3-b]pyrazin-2(1H)-one, or (R)-6-(4-(1H-1,2,4-triazol-5-yl)phenyl)-3-(cyclohexylmethyl)-3,4-dihydropyrazino[2,3-b]pyrazin-2(1H)-one.