2-Chloro-5-methoxy-4-pyrimidinamine

Synthesis of 2-chloro-5-methoxypyrimidin-4-amine [0345] To a stirred solution of 2, 4-dichloro-5-methoxypyrimidine (10 g, 56.17 mmol) in 1, 4-dioxane (20 mL) under argon atmosphere was added ammonium hydroxide (25.5 mL) at RT. The reaction was heated to 100 °C for 21 h in a sealed tube. After completion of reaction (monitored by TLC), the volatile components were removed in vacuo. The crude material was purified by silica gel column chromatography using 40percent EtOAc:hexanes to afford 2-chloro-5-methoxypyrimidin-4-amine (8.9 g, 99percent) as an off-white solid. 1H-NMR (DMSO-< To 2, 4-dichloro-5-methoxypyrimidine (65; 9.8 g, 55 mmol) in dioxane (20 mL) was added 25percent ammonium hydroxide (25 mL). The resulting reaction mixture was heated to 1 00 °C for 21 h in a sealed tube. After cooling, - the solvent was removed under vacuum and the residue was purified by column chromatography to obtain 2-chloi -5-methoxypyrimidin-4-amine (66; 8.3 1 g, 95percent yield). MS (ESI) calcd for C2, 4-Dichloro-5-methoxypyrimidine (10 g, 55.86 mmol) was dissolved in 1, 4- dioxane (20 mL) in a pressure tube and 15M aqueous ammonium hydroxide solution (26 mL) was added. The tube was sealed and heated at 100°C, with stirring, for 18 h. The reaction mixture was cooled and the solid which formed was filtered. The reaction mixture was diluted using ethyl acetate, then washed with water (2 x 20 mL) and brine(20 mL). The organic phases were recombined, dried over sodium sulfate and concentrated in vacuo. Trituration in diethyl ether afforded the title compound (7.77 g, 87percent) as a fluffy solid. H (500 MHz, DMSO-d6) 3.81 (3H, s), 7.10 (1H, br s), 7.42 (1H, br s), 7.68 (1H, s). LCMS m/z 160.2, 4-dichloro-5-methoxy-pyrimidine (100g) is dissolved in methanol, the reaction of ammonia gas at room temperature 24 hours. Reaction solution to dryness under reduced pressure, obtaining white solid, by adding petroleum ether/ethyl acetate (the 10 [...] 1) beating 3-5 time, suction filtration, the white solid obtained 61 g.30 mg Step-1: (S)-3-(1-((4-Amino-5-methoxypyrimidin-2-yl)amino)ethyl)-6-chloroquinolin- 2(1H)-one [0165] A mixture of A mixture of A mixture of A mixture of

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