N-(tert-Butyl)-6-chloropyrimidin-4-amine synthesis

Yield:945896-38-8 90%

Reaction Conditions:

with N-ethyl-N,N-diisopropylamine in isopropyl alcohol at 90; for 12 h;

Steps:

20.20a

Example 20 TV⁴ -tert-Butyl-N⁶-(4-methoxyphenyl)pyrimidine-4,6-diamine 20a. N-tert-Butyl-6-chloropyrimidin-4-amine 251 mg of 4,6-dichloropyrimidine , 123 mg of 2-methylpropan-2-amine and 260 mg of DIPEA were dissolved in 2.5 mL of i-PrOH and charged into a screw cap vial and the vial obtained was kept overnight in a heating block at 90°C. The reaction was monitored by TLC and was completed after 12 hours. The mixture obtained was cooled to r.t., solvent was evaporated and pure N-tert-butyl-6-chloropyrimidin-4-amine was obtained by column chromatography using PE: EtOAc 10: 1. Yield: 90% of theory. NMR (CDC1₃, 200MHz): δ = 1.43 (s, 9H), 4.93-5.19 (bs, 1H), 7.26 (s, 1H), 8.31 (s,1H).¹³C NMR (CDCb, 50MHz): 5 = 28.9 (q), 51.8 (s), 103.6 (d), 158.2 (d), 158.9 (s), 162.6 (s).

References:

WO2011/79343,2011,A2 Location in patent:Page/Page column 37-38