2-Methyl-2-thiopseudourea sulfate → Methyl 4-tert-butyl-2-(methylsulfanyl)pyrimidine-5-carboxylate

HRID 38760

Reaction equation

[CH3:1][C:2]([CH3:11])([CH3:10])[C:3](=O)[CH2:4][C:5]([O:7][CH3:8])=[O:6].[CH3:12]OC(OC)N(C)C.S(O)(O)(=O)=O.[CH3:25][S:26][C:27](=[NH:29])[NH2:28].C([O-])(=O)C.[Na+]>O.CN(C)C=O>[C:2]([C:3]1[C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:12][N:28]=[C:27]([S:26][CH3:25])[N:29]=1)([CH3:11])([CH3:10])[CH3:1]

Participants

Conditions

Temperature: 75 °C

Procedure

A mixture of methyl 4,4-dimethyl-3-oxopentanoate (10 g) and N,N-dimethyl formamide dimethyl acetal (9.5 mL) was stirred at 75° C. for 2 hours. To the reaction mixture were added N,N-dimethyl formamide (100 mL), S-methylisothiourea sulfate (2:1) (9.7 g), and sodium acetate (11.4 g), followed by stirring at 90° C. for 15 hours. The reaction mixture was cooled to room temperature, and water was added thereto. The aqueous layer was extracted with ethyl acetate and the organic layer was washed with water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, then filtered, and concentrated. The obtained residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate) to obtain methyl 4-tert-butyl-2-(methylsulfanyl)pyrimidine-5-carboxylate (8.4 g) as a colorless oily substance.

Workup

stirringby stirring at 90° C. for 15 hours
temperatureThe reaction mixture was cooled to room temperature
extractionThe aqueous layer was extracted with ethyl acetate
washthe organic layer was washed with water and saturated brine
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
filtrationfiltered
concentrationconcentrated
customThe obtained residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate)

Sources & evidence

ORD record: ord-cf7b38d4db5847fe91ef4f679d98c286
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08524727B2

Linked notes

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