Acetone → 2-(4-Chloro-2,6-dimethoxy-pyrimidin-5-yl)-propan-2-ol

HRID 426282Notes

Reaction equation

Br[C:2]1[C:3]([Cl:12])=[N:4][C:5]([O:10][CH3:11])=[N:6][C:7]=1[O:8][CH3:9].C([Li])CCC.[CH3:18][C:19]([CH3:21])=[O:20]>C1COCC1>[Cl:12][C:3]1[C:2]([C:19]([OH:20])([CH3:21])[CH3:18])=[C:7]([O:8][CH3:9])[N:6]=[C:5]([O:10][CH3:11])[N:4]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 5-Bromo-4-chloro-2,6-dimethoxy-pyrimidine (0.546 g, 2.16 mmol) in THF (22 mL) at −78° C. was added n-butyllithium (1.6 M in hexanes, 1.48 mL, 2.37 mmol) over 2 min. Reaction mixture was stirred from 45 min at −78° C., then acetone (0.31 mL, 4.32 mmol) was added. Reaction mixture was stirred for 1 h at −78° C., then quenched with saturated ammonium chloride solution and extracted with ethyl acetate. Organic layer was washed with saturated ammonium chloride solution, dried (MgSO4), concentrated and purified by flash column chromatography (silica gel, 10 to 30% ethyl acetate/hexane) to give a colorless oil (0.275 g, 55%). 1H NMR (300 MHz, CDCl3): δ 3.97 (br s, 1H), 3.92 (s, 3H), 3.82 (s, 3H), 1.54 (s, 6H). Mass spectrum: 233.0, 235.0 (M+H)+.

Workup

customReaction mixture
customReaction mixture
stirringwas stirred for 1 h at −78° C.
customquenched with saturated ammonium chloride solution
extractionextracted with ethyl acetate
washOrganic layer was washed with saturated ammonium chloride solution
dry with materialdried (MgSO4)
concentrationconcentrated
custompurified by flash column chromatography (silica gel, 10 to 30% ethyl acetate/hexane)

Sources & evidence

ORD record: ord-a9ab288c0278407bbf226a81c73ac7db
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08106064B2

Reaction notes

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