N-(3-Aminopropyl)morpholine → HCID 55065471, compound

To 2,4-dichloropyrimidine (5.0 g, 33.5 mmol), diisopropylethylamine (5.85 ml, 33.5 mmol) in 50 mL of a 1:1 mixture of n-BuOH—H2O (1:1) is added 3-morpholinopropan-1-amine (4.90 mL, 33.5 mmol). The resulting mixture is stirred for 18 hours at room temperature. The mixture is then concentrated in vacuo, diluted with 30 mL H2O and extracted with EtOAc (3×75 mL). Combined organic layers are washed with saturated aqueous NaHCO3 (2×75 mL), saturated aqueous NaCl (2×75 mL), and dried (MgSO4). The residue is purified over silica (25% EtOAc in hexanes) to afford 4.5 g (53% yield) of the desired compound. 1H NMR (CDCl3, 300 MHz): δ 1.81 (m, 2H), 2.43-2.62 (m, 6H), 3.30 (m, 2H), 3.79-3.94 (m, 4H), 6.23 (d, J=5.4 Hz, 1H), 6.92 (bs, 1H), 7.99 (bs, 1H). MS (ESI, pos. ion) m/z: 257 (M+1).

1. concentrationThe mixture is then concentrated in vacuo
2. additiondiluted with 30 mL H2O
3. extractionextracted with EtOAc (3×75 mL)
4. washCombined organic layers are washed with saturated aqueous NaHCO3 (2×75 mL), saturated aqueous NaCl (2×75 mL)
5. dry with materialdried (MgSO4)
6. customThe residue is purified over silica (25% EtOAc in hexanes)

ORD record

ord-628a6fdf14da4d28b752c5669dab82a6

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08354407B2