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

HRID 1830516Notes

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-46a8b2273b6a4f6388b0666aff7cf514
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07067514B2

Reaction notes

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