1-Butanol → HCID 55065471, compound

To 2,4-dichloropyrimidine (5.0 g, 33.5 mmol), diisoproylethylamine (5.85 ml, 33.5 mmol) in 50 ml of a 1:1 mixture of n-butanol and water is added 3-morpholinopropan-1-amine (4.90 ml, 33.5 mmol). The resulting mixture was stirred for 18 hours at room temperature. The mixture is then concentrated in vacuo, diluted with 30 mL water and extracted with EtOAc (3×50 ml). Combined organic layers are washed with saturated NaHCO3 (2×20 ml) and saturated NaCl (2×20 ml), then dried over magnesium sulfate. The residue is purified over silica (25% EtOAc in Hexanes) to afford 4.5 g (51% yield) of the desired product. 1H NMR (CDCl3, 300 MHz): δ(ppm) 1.83 (q, J=2.0 Hz, 2H), 2.54 (m, 6H), 3.53 (bs, 2H), 3.79 (t, J=4.7 Hz, 4H), 6.24 (d, J=5.67 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 water
3. extractionextracted with EtOAc (3×50 ml)
4. washCombined organic layers are washed with saturated NaHCO3 (2×20 ml) and saturated NaCl (2×20 ml)
5. dry with materialdried over magnesium sulfate
6. customThe residue is purified over silica (25% EtOAc in Hexanes)

ORD record

ord-af88fcc0318c4c78904909731f54e5d4

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08354407B2