p-Toluenesulfonic acid monohydrate → 4-(3-Iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)-2-(methylthio)pyrimidine

HRID 1889230Notes

Reaction equation

HRID 1889230 reaction equation
[I:1][C:2]1[C:6]([C:7]2[CH:12]=[CH:11][N:10]=[C:9]([S:13][CH3:14])[N:8]=2)=[CH:5][NH:4][N:3]=1.[OH2:15].[C:16]1(C)C=[CH:20][C:19](S(O)(=O)=O)=[CH:18][CH:17]=1>O1C=CCCC1.C(OCC)(=O)C>[I:1][C:2]1[C:6]([C:7]2[CH:12]=[CH:11][N:10]=[C:9]([S:13][CH3:14])[N:8]=2)=[CH:5][N:4]([CH:20]2[CH2:19][CH2:18][CH2:17][CH2:16][O:15]2)[N:3]=1

Participants

5

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 468641604-(5-Iodo-1H-pyrazol-4-yl)-2-(methylsulfanyl)pyrimidine

Product 1

HCID 594244104-(3-Iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)-2-(methylthio)pyrimidine

Reagents, catalysts & solvents 2

HCID 80803,4-dihydro-2H-pyranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-(3-iodo-1H-pyrazol-4-yl)-2-(methylthio)pyrimidine (270 mg, 0.85 mmol) and p-toluenesulfonic acid monohydrate (32 mg, 0.17 mmol) in 3,4-dihydro-2H-pyran (1 ml) was heated at 60° C. for 5 h. The cooled mixture was diluted with ethyl acetate, and the mixture was washed with water and brine, and then dried over sodium sulfate, filtered, and concentrated. The residue was chromatographed on silica gel (10% ethyl acetate in hexanes eluant) to provide the title compound. MS (m/z): 402.7 (M+1).

Workup

  1. washthe mixture was washed with water and brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was chromatographed on silica gel (10% ethyl acetate in hexanes eluant)

Sources & evidence

ORD record
ord-077f67778e4a4391b1eec9db2fe0f78c
Source dataset
uspto-grants-2013_08
Patent number
US08501758B2

Reaction notes

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