Dichloromethane → 4-{2-Chloro-6-[(phenylsulfonyl)methyl]pyrimidin-4-yl}morpholine
Reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([CH2:9][S:10]([CH:13]([CH3:15])[CH3:14])(=[O:12])=[O:11])[N:3]=1.C(N([CH2:21][CH3:22])CC)C.[NH:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1.[CH2:29](Cl)Cl>>[Cl:1][C:2]1[N:7]=[C:6]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[CH:5]=[C:4]([CH2:9][S:10]([C:13]2[CH:15]=[CH:22][CH:21]=[CH:29][CH:14]=2)(=[O:12])=[O:11])[N:3]=1Participants
5
Conditions
- Temperature
- -5 °C
Procedure
2,4-Dichloro-6-[(isopropylsulfonyl)methyl]pyrimidine (2.65 g, 9.85 mmol) was dissolved in DCM (50 mL) and stirred (under nitrogen) at −5° C. Triethylamine (1.5 mL, 10.84 mmol) was added to give a clear brown solution. Morpholine (0.86 mL, 9.85 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 (2.5 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-e458a8f0e78d4ad983065cf88a0ce343
- Source dataset
- uspto-grants-2010_07
- Patent number
- US07750003B2
Reaction notes
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