Cyclopropylamine → 2-chloro-N-cyclopropylfuro[3,2-d]pyrimidin-4-amine

2,4-Dichlorofuro[3,2-d]pyrimidine (30 g, 159 mmol, ArkPharm) was stirred in 1,4-dioxane (330 mL). TEA (26.5 mL, 190 mmol) and cyclopropylamine (12.2 mL, 175 mmol) were added and the mixture stirred at rt overnight. The mixture was diluted with EtOAc (500 mL) and washed with saturated aqueous NaHCO3 (400 mL). The aqueous layer was extracted with EtOAc (2×150 mL). The organic layers were combined, dried with anhydrous MgSO4, filtered, and concentrated in vacuo. The residue was suspended in water (400 mL) and allowed to stir at rt for about 1 h. The suspension was filtered and the solid was dried in a vacuum oven at about 70° C. overnight to give 2-chloro-N-cyclopropylfuro[3,2-d]pyrimidin-4-amine (31.9 g, 96%); LC/MS (Table 2, Method c) Rt=1.58 min.; MS m/z: 210 (M+H)+, 1H NMR (400 MHz, CDCl3) δ 7.77 (d, J=2.1 Hz, 1H), 6.79 (d, J=2.1 Hz, 1H), 5.57-5.50 (m, 1H), 3.12-3.01 (m, 1H), 1.02-0.88 (m, 2H), 0.77-0.65 (m, 2H).

1. washwashed with saturated aqueous NaHCO3 (400 mL)
2. extractionThe aqueous layer was extracted with EtOAc (2×150 mL)
3. dry with materialdried with anhydrous MgSO4
4. filtrationfiltered
5. concentrationconcentrated in vacuo
6. stirringto stir at rt for about 1 h
7. filtrationThe suspension was filtered
8. customthe solid was dried in a vacuum oven at about 70° C. overnight

ORD record

ord-7c75a48f775043329881db53e578c4e5

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08551981B2