2-(Methanesulfonyl)pyrimidine → HCID 11335536, compound

HRID 898323Notes

Reaction equation

HRID 898323 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[CH:9]([NH2:15])[CH2:8][CH2:7][CH2:6][C:5]2=1.CS([C:20]1[N:25]=[CH:24][CH:23]=[CH:22][N:21]=1)(=O)=O>CN(C)C=O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[CH:9]([NH:15][C:20]3[N:25]=[CH:24][CH:23]=[CH:22][N:21]=3)[CH2:8][CH2:7][CH2:6][C:5]2=1

Participants

5

Reactant 2

HCID 132892252-(Methanesulfonyl)pyrimidineHCID 177434976-Chloro-2,3,4,9-tetrahydro-1H-carbazol-1-amine

Product 1

HCID 11335536HCID 11335536, compoundYield 12%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 6-chloro-2,3,4,9-tetrahydro-1H-carbazol-1-amine (50 mg, 0.23 mmol) and 2-methylsulfonylpyrimidine (69 mg, 0.44 mmol) in N,N-dimethylformamide (0.50 mL) was heated at 150° C. for 900 seconds in a Smith Synthesizer microwave. The mixture was diluted with ethyl acetate and extracted with 5% aqueous lithium chloride. The organic layer was isolated and concentrated onto silica. Purification by flash chromatography (0-30% ethyl acetate-hexanes) yielded 6-chloro-N-pyrimidin-2-yl-2,3,4,9-tetrahydro-1H-carbazol-1-amine (8 mg, 12% yield) as a yellow solid.

Workup

  1. extractionextracted with 5% aqueous lithium chloride
  2. customThe organic layer was isolated
  3. concentrationconcentrated onto silica
  4. customPurification by flash chromatography (0-30% ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-e3342028d8f54e9593dc712b6d6ae4ab
Source dataset
uspto-grants-2008_04
Patent number
US07351733B2

Reaction notes

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