Triethylamine → 4-(benzenesulfonylmethyl)-2-chloro-6-[(3S)-3-methylmorpholin-4-yl]pyrimidine
Reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([CH2:9][S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH: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>C(Cl)Cl>[Cl:1][C:2]1[N:7]=[C:6]([N:28]2[CH2:29][CH2:30][O:31][CH2:32][C@@H:27]2[CH3:26])[CH:5]=[C:4]([CH2:9][S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)(=[O:12])=[O:11])[N:3]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -5 °C
Procedure
2,4-dichloro-6-[(phenylsulfonyl)methyl]pyrimidine (2.8 g, 9.24 mmol) was dissolved in DCM (20 mL) and stirred (under nitrogen) at −5° C. Triethylamine (1.42 mL, 10.17 mmol) was added to give a clear brown solution. (3S)-3-methylmorpholine (935 mg, 9.24 mmol) was dissolved in DCM and added dropwise keeping the reaction below −5° C. The cooling bath was then removed and the reaction mixture stirred at room temperature for 1 hour. The reaction mixture was then washed with water (50 mL), dried over magnesium sulphate, filtered and concentrated in vacuo. The crude material was chromatographed on silica, eluting with 0-50% ethyl acetate in DCM to give the desired material as a white solid (2.6 g).
Workup
- customto give a clear brown solution
- additionadded dropwise
- customthe reaction below −5° C
- customThe cooling bath was then removed
- stirringthe reaction mixture stirred at room temperature for 1 hour
- washThe reaction mixture was then washed with water (50 mL)
- dry with materialdried over magnesium sulphate
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe crude material was chromatographed on silica
- washeluting with 0-50% ethyl acetate in DCM
Sources & evidence
- ORD record
- ord-f578864cce054f9ca875b3ec95c29f31
- Source dataset
- uspto-grants-2010_07
- Patent number
- US07750003B2
Reaction notes
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