2-Chloro-4-MethoxypyriMidin-5-aMine

Preparation 164 5.4Msodium methoxide (100 μ, 0.54 mmol) was added dropwise to a stirring solutionof 2, 4-dichloropyrimidin-5 -amine (89 mg, 0.54 mmol) in methanol (2 mL) at 0 °Cunder nitrogen. The reaction was allowed to warm to room temperature andstirred for 1 hr. The reaction was treated with more 5.4M sodium methoxide (10μ) and stirred for a further 1 hr, then left to stand at room temperature for64 hrs. The reaction was quenched with acetic acid (1 mL) and concentrated invacuo. The residue was dissolved in EtOAc (20 mL) and washed with saturatedaqueous NaHC0A mixture of 2, 4-dichloropyrimidin-5-amine (0.5 g, 3.04 mmol), sodium methoxide (0.66 g, 12.19 mmol) and methanol (10 ml) was refluxed for 16 hours. The solvent was removed under reduced pressure. Water was added and the aqueous phase was extracted with ethyl acetate. The organic phase was washed with water and brine, dried over sodium sulphate and concentrated under reduced pressure. The yield of 2-chloro-4-methoxypyrimidin-5-amine after flash chromatography (100-200 mesh size silica gel, 20-25percent ethyl acetate in hexane) was 0.35 g. N-Bromosuccinimide (67 mg, 0.37 mmol) was added to a solution of 2-chloro-4-methoxypyrimidin-5-amine (50 mg, 0.31 mmol) in chloroform (2 ml) and the resulting mixture was stirred at RT for 3 hours. Water was added and the mixture extracted with chloroform. The organic phase was washed with water and brine, dried over sodium sulphate and concentrated under reduced pressure. The yield of 4-bromo-2-chloro-6-methoxypyrimidin-5-amine was 60 mg.Preparation 164: 2-Chloro-4-methoxypyrimidin-5-amine; [00336] Sodium methoxide (0.5M in methanol, 3.7ml_, 1 .829mmol) was added to a solution of 2, 4-dichloropyrimidin-5-amine (0.2g, 1 .220mmol) in MeOH (2.5ml_). The reaction was stirred at room temperature for 1 .5 hours. The reaction was then diluted with EtOAc and quenched with water. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were dried (NaPreparation 164 5.4Msodium methoxide (100 μ, 0.54 mmol) was added dropwise to a stirring solutionof 2, 4-dichloropyrimidin-5 -amine (89 mg, 0.54 mmol) in methanol (2 mL) at 0 °Cunder nitrogen. The reaction was allowed to warm to room temperature andstirred for 1 hr. The reaction was treated with more 5.4M sodium methoxide (10μ) and stirred for a further 1 hr, then left to stand at room temperature for64 hrs. The reaction was quenched with acetic acid (1 mL) and concentrated invacuo. The residue was dissolved in EtOAc (20 mL) and washed with saturatedaqueous NaHC0A mixture of 2, 4-dichloropyrimidin-5-amine (0.5 g, 3.04 mmol), sodium methoxide (0.66 g, 12.19 mmol) and methanol (10 ml) was refluxed for 16 hours. The solvent was removed under reduced pressure. Water was added and the aqueous phase was extracted with ethyl acetate. The organic phase was washed with water and brine, dried over sodium sulphate and concentrated under reduced pressure. The yield of 2-chloro-4-methoxypyrimidin-5-amine after flash chromatography (100-200 mesh size silica gel, 20-25percent ethyl acetate in hexane) was 0.35 g. N-Bromosuccinimide (67 mg, 0.37 mmol) was added to a solution of 2-chloro-4-methoxypyrimidin-5-amine (50 mg, 0.31 mmol) in chloroform (2 ml) and the resulting mixture was stirred at RT for 3 hours. Water was added and the mixture extracted with chloroform. The organic phase was washed with water and brine, dried over sodium sulphate and concentrated under reduced pressure. The yield of 4-bromo-2-chloro-6-methoxypyrimidin-5-amine was 60 mg.Preparation 164: 2-Chloro-4-methoxypyrimidin-5-amine; [00336] Sodium methoxide (0.5M in methanol, 3.7ml_, 1 .829mmol) was added to a solution of 2, 4-dichloropyrimidin-5-amine (0.2g, 1 .220mmol) in MeOH (2.5ml_). The reaction was stirred at room temperature for 1 .5 hours. The reaction was then diluted with EtOAc and quenched with water. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were dried (Na

Molecular Weight:159.57
XLogP3:0.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:159.0199395
Monoisotopic Mass:159.0199395
Topological Polar Surface Area:61
Heavy Atom Count:10
Complexity:113
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes