ETHYL 5-AMINO-6-(METHYLAMINO)PYRIMIDINE-4-CARBOXYLATE synthesis

Yield:1095823-03-2 18%

Reaction Conditions:

with N-ethyl-N,N-diisopropylamine;dichloro bis(acetonitrile) palladium(II);2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl in acetonitrile at 130; under 6205.94 Torr; for 4 h;

Steps:

21

Synthesis of Compound 21.1. A mixture of compound 11.1 (1.5 g, 9.4 mmol), BINAP (1 g, 2 mmol), bis(acetonitrile)palladium(II) chloride (0.450 g, 1.73 mmol), DIEA (1.97 mL, 11.3 mmol) and EtOH (22 mL) in MeCN (22 mL) was heated (130° C.) under CO (120 psi). After 4 hr, the reaction was filtered through celite, and the solvent was removed in vacuo. The residue was purified by flash chromatography using DCM/EtOAc (SiO₂, 100/0 to 0/100) as eluant to afford compound 21.1 (338 mg, 18%) as a yellow solid. ¹H NMR (300 MHz, DMSO-d₆) δ 7.88 (s, 1H), 7.19 (q, J=4.5 Hz, 1H), 6.43 (br. s., 2H), 4.26 (q, J=7.2 Hz, 2H), 2.91 (d, J=4.5 Hz, 3H), 1.29 (t, J=7.2 Hz, 3H)

References:

US2009/5359,2009,A1 Location in patent:Page/Page column 28