tert-Butyl carbamate → Methyl 5-((tert-butoxycarbonyl)amino)pyrimidine-2-carboxylate

Temperature

90 °C

The methyl 5-bromopyrimidine-2-carboxylate (1 g, 4.61 mmol), tert-butyl carbamate (0.756 g, 6.45 mmol), diacetoxypalladium (0.052 g, 0.23 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.267 g, 0.46 mmol), cesium carbonate (2.252 g, 6.91 mmol) and dioxane (15 mL) were placed and sealed into a microwave tube. The reaction was degased, purged with argon and heated to 90 °C (oil bath) over a period of 7 hours . The mixture was poured in water, extracted with ethyl acetate (x2). The organic phase was washed with brine, dried over magnesium sulfate and concentrated. The crude product was purified by flash chromatography on silica gel 15-40µm eluting with 5 to 50% ethyl acetate in petroleum ether. The solvent was evaporated to dryness to afford methyl 5-(tert- butoxycarbonylamino)pyrimidine-2-carboxylate (0.710 g, 60.8 %) as a white solid.

ORD record

ord-e89c2aa0807f47eabc561a9b2db7adf0

Source dataset

750 AstraZeneca ELN dataset

Original link

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