Water → 2-(4,6-Dimethoxypyrimidine-2-yl)acetonitrile

HRID 404540Notes

Reaction equation

[C:1]([CH:3]([C:11]1[N:16]=[C:15]([O:17][CH3:18])[CH:14]=[C:13]([O:19][CH3:20])[N:12]=1)C(OC(C)(C)C)=O)#[N:2].C1(C)C=CC=CC=1.CS(O)(=O)=O.O>C(OCC)(=O)C>[C:1]([CH2:3][C:11]1[N:12]=[C:13]([O:19][CH3:20])[CH:14]=[C:15]([O:17][CH3:18])[N:16]=1)#[N:2]

Participants

Conditions

Temperature: 100 °C

Procedure

Into a 50-ml eggplant-shaped flask provided with a magnetic stirrer and a reflux condenser were added 2.79 g (10 mmol) of tert-butyl 2-cyano-2-(4,6-dimethoxypyrimidin-2-yl)acetate, 10 ml of toluene and then 0.38 g (4 mmol) of methanesulfonic acid. The system inside was purged with nitrogen and stirred for 2 hours at 100° C. After the completion of a reaction, the system was cooled to room temperature; 30 ml water and 30 ml of ethyl acetate were added for phase separation; and re-extraction was conducted using 20 ml of ethyl acetate. Two ethyl acetate phases were combined, washed with saturated sodium chloride water, and dried over anhydrous sodium sulfate. Then, ethyl acetate was distilled off under reduced pressure to obtain 2-cyanomethyl-4,6-dimethoxypyrimidine as white crystal of 1.45 g. HPLC purity: 95.7% Yield: 81%

Workup

customInto a 50-ml eggplant-shaped flask provided with a magnetic stirrer and a reflux condenser
customThe system inside was purged with nitrogen
customAfter the completion of a reaction
temperaturethe system was cooled to room temperature
extractionand re-extraction
washwashed with saturated sodium chloride water
dry with materialdried over anhydrous sodium sulfate
distillationThen, ethyl acetate was distilled off under reduced pressure

Sources & evidence

ORD record: ord-15eeb50f2eed4a75bef0a3fed91f25b9
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08748605B2

Reaction notes

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