Morpholine → 4-{2-Chloro-6-[(phenylsulfonyl)methyl]pyrimidin-4-yl}morpholine

HRID 2353655Notes

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.[NH:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1>C(Cl)Cl>[Cl:1][C:2]1[N:7]=[C:6]([N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)[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

Participants

Conditions

Temperature: -5 °C

Procedure

2,4-dichloro-6-[(phenylsulfonyl)methyl]pyrimidine (6 g, 19.8 mmol) was dissolved in DCM (50 mL) and stirred (under nitrogen) at −5° C. Triethylamine (3.06 mL, 21.8 mmol) was added to give a clear brown solution. Morpholine (1.65 mL, 19.8 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 (4 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-ae827812c6604e2c915909b3334990b7
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07750003B2

Reaction notes

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