p-Toluenesulfonic acid monohydrate → HCID 59424410, compound

HRID 629488Notes

Reaction equation

HRID 629488 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 59424410HCID 59424410, compound

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-2f768d4f5968491395ed29dff2bbb9b0
Source dataset
uspto-grants-2016_04
Patent number
US09314464B2

Reaction notes

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