Water → HCID 59380224, compound
Reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([CH2:9][S:10]([CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)(=[O:12])=[O:11])[N:3]=1.C(N(CC)CC)C.[CH3:26][C@H:27]1[CH2:32][O:31][CH2:30][CH2:29][NH:28]1.O>C(Cl)Cl>[Cl:1][C:2]1[N:3]=[C:4]([CH2:9][S:10]([CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)(=[O:12])=[O:11])[CH:5]=[C:6]([N:28]2[CH2:29][CH2:30][O:31][CH2:32][C@@H:27]2[CH3:26])[N:7]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 6 °C
Procedure
To a cooled (ice/water bath) solution of 2,4-dichloro-6-(cyclohexylsulfonylmethyl)pyrimidine (1.65 g, 5.34 mmol) in DCM (25 mL) was added triethylamine (0.820 mL, 5.88 mmol). The resulting solution was treated, dropwise over 8 minutes, with a solution of (3S)-3-methylmorpholine (609 mg, 6.02 mmol) in DCM (5 mL). The mixture was stirred at 6° C. for 30 minutes. The cooling bath was then removed and reaction mixture left to stir overnight. Water (25 mL) was then added and reaction mixture stirred for 5 minutes. The organic layer was then separated, dried (MgSO4) and evaporated to give a crude brown oil, which was purified by flash silica chromatography, elution gradient 25 to 75% ethyl acetate in isohexane, to give the desired material (1.440 g).
Workup
- customThe cooling bath was then removed
- customreaction mixture
- waitleft
- stirringto stir overnight
- customreaction mixture
- stirringstirred for 5 minutes
- customThe organic layer was then separated
- dry with materialdried (MgSO4)
- customevaporated
- customto give a crude brown oil, which
- customwas purified by flash silica chromatography, elution gradient 25 to 75% ethyl acetate in isohexane
Sources & evidence
- ORD record
- ord-5e1bbc4b72bf47c5a3febd38e9e8e952
- Source dataset
- uspto-grants-2010_07
- Patent number
- US07750003B2
Reaction notes
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