Triethylamine → HCID 58504423, compound

Temperature

120 °C

To 4,6-dichloro-2-pyrimidinamine (500 mg, 3.05 mmol) in CH3OH (10 mL) were added (3R)-3-methylmorpholine hydrochloride (441 mg, 3.2 mmol) and triethylamine (1.28 mL, 9.2 mmol), and the reaction mixture was heated in a microwave at 120° C. for 35 minutes. Side-product started to form. An additional 0.5 eq of (3R)-3-methylmorpholine hydrochloride and 0.2 mL of triethylamine were added, and the mixture was heated in an oil bath at 50° C. for 3 days and in a microwave at 100° C. for 3 hours. The mixture was cooled down, evaporated under vacuum, and the resulting residue was partitioned between EtOAc and water, and extracted with EtOAc (2×) and CH2Cl2 (2×). The combined organics were washed with water and brine, dried (MgSO4), filtered, and evaporated. The resulting material was triturated with Et2O and dried in vacuo to afford the title compound (524 mg). LC-MS (ES) m/z=229, 231 [M+H]+.

1. customto form
2. temperaturethe mixture was heated in an oil bath at 50° C. for 3 days and in a microwave at 100° C. for 3 hours
3. temperatureThe mixture was cooled down
4. customevaporated under vacuum
5. customthe resulting residue was partitioned between EtOAc and water
6. extractionextracted with EtOAc (2×) and CH2Cl2 (2×)
7. washThe combined organics were washed with water and brine
8. dry with materialdried (MgSO4)
9. filtrationfiltered
10. customevaporated
11. customThe resulting material was triturated with Et2O
12. customdried in vacuo

ORD record

ord-ce999d9f1dcf4cb2b1d3ba6768fffac4

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08697685B2