4-Amino-2-ethylsulfanylpyrimidine-5-carboxylic acid methoxymethylamide → HCID 10039812, compound
Reaction equation
COCN[C:5]([C:7]1[C:8]([NH2:16])=[N:9][C:10]([S:13][CH2:14][CH3:15])=[N:11][CH:12]=1)=[O:6].[CH3:17][O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[Li]>O1CCCC1>[NH2:16][C:8]1[C:7]([C:5]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[O:18][CH3:17])=[O:6])=[CH:12][N:11]=[C:10]([S:13][CH2:14][CH3:15])[N:9]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
4-Amino-2-ethylsulfanylpyrimidine-5-carboxylic acid methoxymethylamide (200 mg, 0.830 mmol, Example 1) was dissolved in anhydrous tetrahydrofuran (3 mL) and cooled to −78° C. A solution of 2-methoxyphenyl lithium (˜3 equiv, freshly prepared following the same procedure as Step A of Example 2) was added. The reaction was stirred at −78° C. for 1.5 hours and quenched with aqueous ammonium chloride solution. The resulting mixture was 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 60:40 of hexane/ethyl acetate to give (4-amino-2-ethylsulfanylpyrimidin-5-yl)-(2-methoxy-phenyl)-methanone as a white solid (224.1 mg, 94% yield). HRMS, observed: 290.0961; Calcd for (M+H)+: 290.0958.
Workup
- additionwas added
- customquenched with aqueous ammonium chloride solution
- extractionThe resulting mixture was extracted 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 60:40 of hexane/ethyl acetate
Sources & evidence
- ORD record
- ord-fa434ec979424feeb15a69d7fbb27939
- Source dataset
- uspto-grants-2007_01
- Patent number
- US07157455B2
Reaction notes
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