2-(4-amino-N-methylanilino)ethanol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (4E)-6-bromo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione (0.17 g, 0.61 mmol) and 2-[(4-amino-phenyl)-methyl-amino]-ethanol (0.10 g, 0.61 mmol) were stirred in N,N-dimethylformamide (3 mL) and triethylamine (0.16 mL) at 60-70° C. The reaction mixture is quenched by the addition of water. The solid material is then collected, washed with diethyl ether, water, and methanol, and then dried under vacuum to give (4Z)-6-bromo-4-[({4-[(2-hydroxyethyl)(methyl)amino]phenyl}amino)methylene]isoquinoline-1,3(2H,4H)-dione (0.16 g, 64%) as a rust colored powder. at 60-70° C The reaction mixture is quenched by the addition of water The solid material is then collected washed with diethyl ether, water, and methanol dried under vacuum

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 2-(methyl-4-nitroanilino)ethanol (0.20 g, 1.0 mmol) in ethanol (25 mL) is hydrogenated for two hours at atmospheric pressure over 10% Pd/C. The mixture is filtered through a pad of diatomaceous earth and concentrated under reduced pressure to give 2-[(4-amino-phenyl)-methyl-amino]-ethanol as a dark oil, which solidified upon standing. The mixture is filtered through a pad of diatomaceous earth concentrated under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 2-(methyl-4-nitroanilino)ethanol (0.20 g, 1.0 mmol) in ethanol (25 mL) is hydrogenated for two hours at atmospheric pressure over 10% Pd/C. The mixture is filtered through a pad of diatomaceous earth and concentrated under reduced pressure to give 2-[(4-amino-phenyl)-methyl-amino]-ethanol as a dark oil, which solidified upon standing. The mixture is filtered through a pad of diatomaceous earth concentrated under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 2-(methyl-4-nitroanilino)ethanol (0.20 g, 1.0 mmol) in ethanol (25 mL) is hydrogenated for two hours at atmospheric pressure over 10% Pd/C. The mixture is filtered through a pad of diatomaceous earth and concentrated under reduced pressure to give 2-[(4-amino-phenyl)-methyl-amino]-ethanol as a dark oil, which solidified upon standing. The mixture is filtered through a pad of diatomaceous earth concentrated under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Using an analogous reaction procedure to that described in Example 6, 6-chloro-4-(3'-chloro-4'-fluoroanilino)pyrimidine (0.258 g) was reacted with 4-[N-(2-hydroxyethyl)-N-methylamino]aniline (0.166 g). The product so obtained was recrystallised from a mixture of methylene chloride, methanol and hexane to give 4-[3'-chloro-4'-fluoroanilino]6-[4'-{N-(2-hydroxyethyl) -N-methylamino}anilino]pyrimidine in 10% yield; an analogous reaction procedure to The product so obtained was recrystallised from a mixture of methylene chloride, methanol and hexane