Diisopropylamine → HCID 22452599, compound
Reaction equation
[CH:1](NC(C)C)(C)C.[CH3:8][S:9][C:10]1[N:15]=[C:14](C)[CH:13]=[CH:12][N:11]=1.CON(C)[C:20](=[O:31])[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=1>C1COCC1>[CH3:8][S:9][C:10]1[N:11]=[CH:12][C:13]([CH2:1][C:20]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=2)=[O:31])=[CH:14][N:15]=1Participants
Conditions
- Temperature
- -78 °C
Procedure
To a solution of diisopropylamine (7.9 mL, 0.056 mole) in THF (100 mL) at −78° C. and under argon was added 2.5M n-butylithium (22.5 mL, 0.056 mole) followed, after 5 minutes, by a solution of 2-methylthio-4-methylpyrimidine (5.27 g, 0.376 mole) in THF (20 mL). Upon stirring for 15 min. at -78° C., a solution of N-methoxy-N-methyl-3-trifluoromethylbenzamide (9.63 g, 0.041 mole) in THF (90 mL) was added. The reaction was allowed to warm to 0° C. and then quenched into water (400 mL) and ethyl acetate (400 mL). The layers were separated and the aqueous layer washed with ethyl acetate (200 mL). The ethyl acetate extracts were combined, dried over anhydrous sodium sulfate, filtered, and concentrated to a solid (11.9 g). Trituration from 10% ether/hexane (100 mL) gave 9.5 g (78%) of the title compound.
Workup
- temperatureto warm to 0° C.
- customquenched into water (400 mL) and ethyl acetate (400 mL)
- customThe layers were separated
- washthe aqueous layer washed with ethyl acetate (200 mL)
- dry with materialdried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated to a solid (11.9 g)
Sources & evidence
- ORD record
- ord-a86373f3d0fb429daf41ac86a569698b
- Source dataset
- uspto-grants-2002_06
- Patent number
- US06403596B1
Reaction notes
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