5-Pyrimidinecarboxamide, 4-amino-2-(ethylthio)-N-methoxy-N-methyl- → HCID 11722738, compound
Reaction equation
CON(C)[C:4]([C:6]1[C:7]([NH2:15])=[N:8][C:9]([S:12][CH2:13][CH3:14])=[N:10][CH:11]=1)=[O:5].[O:17]([C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=1[Li])[CH3:18]>O1CCCC1>[NH2:15][C:7]1[C:6]([C:4]([C:24]2[CH:23]=[C:22]([F:25])[CH:21]=[CH:20][C:19]=2[O:17][CH3:18])=[O:5])=[CH:11][N:10]=[C:9]([S:12][CH2:13][CH3:14])[N:8]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
A solution of 4-amino-2-ethylsulfanyl-pyrimidine-5-carboxylic acid methoxy-methylamide (400 mg, 1.65 mmol, Example 1) was dissolved in anhydrous tetrahydrofuran (6 mL) and cooled to −78° C. A solution of the freshly prepared 2-methoxyl-5-fluorophenyl lithium (˜5 equiv, prepared following the same procedure as described in Step A of Example 2) was added over 10-30 minutes and the orange colored reaction mixture was stirred at −78 to 0° C. for 1-3 hours until the complete consumption of the starting material. The resulting mixture was quenched with aqueous ammonium chloride solution, extracted with ethyl acetate (3×20 mL), washed with brine (2×10 mL), dried over sodium sulfate and evaporated in vacuo. The residue was purified on silica gel with 80/20→60/40 of hexane/ethyl acetate to give (4-amino-2-ethylsulfanyl-pyrimidin-5-yl)-(5-fluoro-2-methoxy-phenyl)-methanone as a white solid (277 mg). MS (M+H)+, 308.
Workup
- additionwas added over 10-30 minutes
- customThe resulting mixture was quenched with aqueous ammonium chloride solution
- extractionextracted with ethyl acetate (3×20 mL)
- washwashed with brine (2×10 mL)
- dry with materialdried over sodium sulfate
- customevaporated in vacuo
- customThe residue was purified on silica gel with 80/20→60/40 of hexane/ethyl acetate
Sources & evidence
- ORD record
- ord-d01b543008e7406fbc99d5f52bd30ea5
- Source dataset
- uspto-grants-2009_11
- Patent number
- US07615634B2
Reaction notes
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