2,2-Difluoroethanamine → HCID 86665115, compound

To a flask was added 2,4-dichlorofuro[3,2-d]pyrimidine (2 g, 10.58 mmol, Arkpharm), DCM (20 mL) and TEA (2.95 mL, 21.16 mmol). A solution of 2,2-difluoroethanamine (0.858 g, 10.6 mmol, Matrix) in DCM (5 mL) was added drop-wise and the mixture was stirred at rt overnight. The mixture was concentrated under reduced pressure. To the residue was added 1,4-dioxane (20 mL), TEA (2.95 mL, 21.2 mmol) and a solution of 2,2-difluoroethanamine (0.858 g, 10.58 mmol, Matrix) in 1,4-dioxane (5 mL). The mixture was stirred at rt for about 4 h, and then at about 55° C. overnight. The mixture was concentrated under reduced pressure, and the residue was taken up in EtOAc (120 mL) and water (25 mL). The organic layer was isolated and washed with water (2×25 mL). The combined aqueous layers were washed with EtOAc (2×25 mL). The combined organic layers were washed with brine (25 mL), dried with MgSO4, filtered, concentrated under reduced pressure, and dried in a vacuum oven at about 70° C. over 2 days to give 2-chloro-N-(2,2-difluoroethyl)furo[3,2-d]pyrimidin-4-amine (2.20 g, 89%): LC/MS (Table 2, Method c) Rt=1.69 min.; MS m/z: 234 (M+H)+.

1. concentrationThe mixture was concentrated under reduced pressure
2. stirringThe mixture was stirred at rt for about 4 h
3. customat about 55° C.
4. customovernight
5. concentrationThe mixture was concentrated under reduced pressure
6. customThe organic layer was isolated
7. washwashed with water (2×25 mL)
8. washThe combined aqueous layers were washed with EtOAc (2×25 mL)
9. washThe combined organic layers were washed with brine (25 mL)
10. dry with materialdried with MgSO4
11. filtrationfiltered
12. concentrationconcentrated under reduced pressure
13. customdried in a vacuum oven at about 70° C. over 2 days

ORD record

ord-f43edf51b1fa490a9db9bb4090effc63

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08551981B2