1-Butanol → 4-(2-Butoxy-6-chloropyrimidin-4-yl)morpholine

HRID 2262457Notes

Reaction equation

[CH2:1]([OH:5])[CH2:2][CH2:3][CH3:4].N#N.[H-].[Na+].Cl[C:11]1[N:16]=[C:15]([Cl:17])[CH:14]=[C:13]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[N:12]=1>CN(C=O)C>[CH2:1]([O:5][C:11]1[N:16]=[C:15]([Cl:17])[CH:14]=[C:13]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[N:12]=1)[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of n-butanol (0.633 g, 8.54 mmol) in anhydrous DMF (50 mL) at 0° C. under the N2, NaH (0.307 g, 12.8 mmol) was added quickly. The obtained suspension was stirred for 0.5 h at 0° C. 2,4-Dichloro-6-(morpholin-4-yl)pyrimidine (2 g, 8.54 mmol) was added to the suspension. After the suspension was warmed to room temperature and stirred for 12 h, the reaction mixture was quenched with ice/brine and extracted with 200 mL EtOAc. The extract was washed with brine, and dried over Na2SO4. The solvent was removed under reduced pressure. The crude residue was purified using flash chromatography (silica; EtOAc/Hexane: 1/6) to yield 1.4 g of 2-n-butoxy-4-chloro-6-(morpholin-4-yl)pyrimidine (white solid, 60%).

Workup

temperatureAfter the suspension was warmed to room temperature
stirringstirred for 12 h
customthe reaction mixture was quenched with ice/brine
extractionextracted with 200 mL EtOAc
washThe extract was washed with brine
dry with materialdried over Na2SO4
customThe solvent was removed under reduced pressure
customThe crude residue was purified

Sources & evidence

ORD record: ord-3b9004ecd153440aa2e2baa95ab5539b
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07851466B2

Reaction notes

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