Hydrochloric Acid → HCID 24777233, compound

Participants

Reaction Steps

In a 3-necked round bottom flask equipped with a thermal couple, an overhead stirrer and a condenser was added 4-amino-6-chloro-pyrimidine-5-carbaldehyde Cpd 1a (3.23 g, 19.0 mmol), 4-benzyloxy-3-chloro-phenylamine Cpd 1b (4.24 g, 18.1 mmol), 2-methoxyethanol (27 ml) and water (3 ml). The mixture was stirred at room temperature and a 6N HCl solution (0.30 ml, 0.10 eq.) was added. The mixture was heated to 80° C. for 1-2 hours until the starting materials were consumed. The mixture was cooled to room temperature and 6 N NaOH solution (3.3 ml) and water (8 ml) were added. The mixture was cooled to room temperature again and the solid was collected by vacuum filtration. The reaction flask was rinsed by 1:1 EtOH:water (2×10 ml) and the rinses were used to wash the filter cake. The filter cake was further washed by 1:1 EtOH:water (2×10 ml), suction dried, dried in an vacuum oven at 60° C. under house vacuum to afford the title Compound 1c free base as a light yellow solid (6.06 g). 1H NMR (400 MHz, DMSO-d6) δ 10.66 (s, 1H), 10.14 (s, 1H), 8.11 (s, 1H), 7.90 (bs, 1H), 7.88 (d, J=2.0 Hz, 1H), 7.48-7.32 (m, 5H), 7.21 (d, J=8.0 Hz, 1H), 5.20 (s, 2H), 3.24 (bs, 2H); mp 206° C. (by DSC).

Provenance & Evidence