Triethylamine → N-(3-(2-chlorothieno[3,2-d]pyrimidin-7-yl)phenyl)methanesulfonamide

HRID 2042209Notes

Reaction equation

HRID 2042209 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[S:10][CH:9]=[C:8]([C:11]3[CH:12]=[C:13]([NH2:17])[CH:14]=[CH:15][CH:16]=3)[C:6]=2[N:7]=1.[CH3:18][S:19](Cl)(=[O:21])=[O:20].C(N(CC)CC)C>O1CCCC1.C(OCC)(=O)C>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[S:10][CH:9]=[C:8]([C:11]3[CH:12]=[C:13]([NH:17][S:19]([CH3:18])(=[O:21])=[O:20])[CH:14]=[CH:15][CH:16]=3)[C:6]=2[N:7]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 866732143-(2-Chlorothieno[3,2-d]pyrimidin-7-yl)benzenamine

Product 1

HCID 86673215N-(3-(2-chlorothieno[3,2-d]pyrimidin-7-yl)phenyl)methanesulfonamideYield 91.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-(2-Chlorothieno[3,2-d]pyrimidin-7-yl)benzenamine (800 mg, 3.06 mmol) was dissolved in anhydrous tetrahydrofuran (15 mL) and methanesulfonyl chloride (0.27 mL, 3.37 mmol) and triethylamine (0.85 mL, 6.13 mmol) were added. The mixture solution was stirred for 2 hours, diluted with ethyl acetate, and then washed with brine. The organic layer was concentrated by drying with magnesium sulfate. Purification by chromatography (10% ethyl acetate/hexane) yielded the target compound (950 mg, 91% yield).

Workup

  1. washwashed with brine
  2. concentrationThe organic layer was concentrated
  3. dry with materialby drying with magnesium sulfate
  4. customPurification by chromatography (10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-5f959c3db4604ab78d4bd3f8a882c3a4
Source dataset
uspto-grants-2013_11
Patent number
US08586580B2

Reaction notes

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