Sodium hydride → HCID 21934704, compound

Participants

Reaction Steps

2-Chloropyrimidin-4-amine 49-1 (0.30 g, 2.32 mmol) and sodium hydride (0.093 g, 2.32 mmol) were suspended in dry THF and stirred for 20 minutes before adding 2-chloro-1,3-thiazole-5-carbonitrile 2-2 (0.33 g, 2.32 mmol) and more sodium hydride (0.093 g, 2.32 mmol) simultaneously. This was refluxed for 1.5 hour and then quenched with methanol and water, and concentrated to dryness. The residue was partitioned between DCM, MeOH, and water. The aqueous layer was evaporated to dryness and then purified on a silica column. 1H-NMR (CD3OD): 8.50(d, 1H); 8.42(s, 1H); 7.11(d, 1H). By 1H-NMR this material is a mixture of the desired product and 2-chloropyrimidin-4-amine in a ratio of 5:8, which was used as is in the next step.

Provenance & Evidence