Dimethylformamide → HCID 69179367, compound

HRID 917374Notes

Reaction equation

CN(C)C=O.[CH3:6][C:7]1[C:12]([C:13]([OH:15])=[O:14])=[CH:11][N:10]=[C:9]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:8]=1.CS(O[CH2:27][CH2:28][C:29]([CH3:33])=[C:30]([F:32])[F:31])(=O)=O.C(=O)([O-])O.[Na+]>O>[CH3:6][C:7]1[C:12]([C:13]([O:15][CH2:27][CH2:28][C:29]([CH3:33])=[C:30]([F:32])[F:31])=[O:14])=[CH:11][N:10]=[C:9]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:8]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To 5 ml of N,N-dimethylformamide were dissolved 0.34 g (1.6 mmol) of 4-methyl-2-phenylpyrimidine-5-carboxylic acid, synthesized in accordance with a method described in “J. Chem. Soc.”, page 2183 (1923), and 0.30 g (1.5 mmol) of 4,4-difluoro-3-methyl-3-butenyl methanesulfonate, followed by the addition of 0.27 g (3.2 mmol) of sodium hydrogencarbonate and stirring at 100° C. for 3 hours. The reaction liquid was then poured in water and extracted with diethtyl ether. The organic layer was washed with water and a saturated saline solution in this order, followed by drying over anhydrous magnesium sulfate and concentration under reduced pressure. The residue was purified with silica gel column chromatography (diisopropyl ether:hexane=1:4) to obtain 0.35 g (yield: 73%) of 4,4-difluoro-3-methyl-3-butenyl 4-methyl-2-phenylpyrimidine-5-carboxylate.

Workup

customsynthesized in accordance with a method
customThe reaction liquid
extractionextracted with diethtyl ether
washThe organic layer was washed with water
dry with materialby drying over anhydrous magnesium sulfate and concentration under reduced pressure
customThe residue was purified with silica gel column chromatography (diisopropyl ether:hexane=1:4)

Sources & evidence

ORD record: ord-d5834e2f2f6d421982344909185c0bdf
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07273878B2

Reaction notes

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