2,4-Dichloropyridine → 5-((2-Chloropyridin-4-yl)oxy)pyrimidin-2-amine

A solution of 2-amino-5-hydroxypyrimidine (1.00 g, 9.00 mmol) in DMA (25 mL) was treated with potassium tert-butoxide (1.24 g, 11.05 mmol). The thick mixture was stirred at room temperature for 1 h. To this was added a solution of 2,4-dichloropyridine (1.21 g, 8.18 mmol) in DMA (10 mL) and the reaction was stirred at RT overnight under Ar. The mixture was diluted with EtOAc (100 mL) and washed with water (100 mL). The organic phase was separated and the aqueous was extracted with EtOAc (100 mL). The combined EtOAc layers were washed with 5% LiCl (100 mL) and brine (100 mL) and then dried over sodium sulfate. The solvents were evaporated at reduced pressure to give 5-((2-chloropyridin-4-yl)oxy)pyrimidin-2-amine as a pale yellow solid (592 mg, 32%). MS (ESI) m/z: 223.0 (M+H+).

1. stirringthe reaction was stirred at RT overnight under Ar
2. washwashed with water (100 mL)
3. customThe organic phase was separated
4. extractionthe aqueous was extracted with EtOAc (100 mL)
5. washThe combined EtOAc layers were washed with 5% LiCl (100 mL) and brine (100 mL)
6. dry with materialdried over sodium sulfate
7. customThe solvents were evaporated at reduced pressure

ORD record

ord-b16567d308ff474ebded485e25d77609

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09133183B2