Water → 2-Chloro-5-[(2,2-dimethyl-1,3-dioxan-5-yl)methoxy]pyrimidine

HRID 632610Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[CH:6][C:5]([OH:8])=[CH:4][N:3]=1.C1(C)C(S(O[CH2:19][CH:20]2[CH2:25][O:24][C:23]([CH3:27])([CH3:26])[O:22][CH2:21]2)(=O)=O)=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN1CCCC1=O>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([O:8][CH2:19][CH:20]2[CH2:25][O:24][C:23]([CH3:27])([CH3:26])[O:22][CH2:21]2)=[CH:4][N:3]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To 2.53 g (19.4 mmol) of 2-chloro-5-hydroxypyrimidine, a solution of 5.95 g (19.8 mmol) of 5-(toluenesulfonyloxymethyl)-2,2-dimethyl-1,3-dioxane in 11 ml of N-methylpyrrolidone and 6.50 g (19.9 mmol) of cesium carbonate were added, and the reaction mixture was stirred at 70° C. for 3.5 hours. After completion of the reaction, the reaction solution was poured into water and extracted with ethyl acetate twice. The obtained organic layers were combined, washed with water and saturated sodium chloride aqueous solution in order and dried with anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. tert-Butyl methyl ether was added to the obtained residue, and the precipitate was obtained by filtration to provide 3.72 g of the title compound as a white solid (yield: 74%).

Workup

customAfter completion of the reaction
extractionextracted with ethyl acetate twice
washwashed with water and saturated sodium chloride aqueous solution in order
dry with materialdried with anhydrous sodium sulfate
distillationthe solvent was distilled off under reduced pressure
additiontert-Butyl methyl ether was added to the obtained residue
customthe precipitate was obtained by filtration

Sources & evidence

ORD record: ord-9351954d48ce44b28736ed86dc206bdd
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321747B2

Reaction notes

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