Thiophenol → 736142-84-0

HRID 222162Notes

Reaction equation

HRID 222162 reaction equation
Cl[C:2]1[N:7]=[CH:6][NH:5][C:4]2=[N:8][CH:9]=[CH:10][C:3]=12.[C:11]1([SH:17])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(O)CCC>[C:11]1([S:17][C:2]2[C:3]3[CH:10]=[CH:9][NH:8][C:4]=3[N:5]=[CH:6][N:7]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 7969ThiophenolHCID 178418725HCID 178418725, compound

Product 1

HCID 11481564736142-84-0Yield 92%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of 4-chloro-1H-pyrrolo[2,3-d]pyrimidine (1.69 g, 11.0 mmol) and TEA (4.60 mL, 33.0 mmol) in 1-butanol (25.0 mL) was added benzenethiol (3.39 mL, 33.0 mmol), and the mixture was refluxed at 140° C. overnight. The reaction was then cooled to rt and concentrated in vacuo. The off-white solid was purified by silica gel chromatography eluting with a gradient of 0 to 35% EtOAc in DCM to afford the product (2.29 g, 92%). LC/MS: Rt=1.55 min, ES+ 228 (FA standard).

Workup

  1. temperatureThe reaction was then cooled to rt
  2. concentrationconcentrated in vacuo
  3. customThe off-white solid was purified by silica gel chromatography
  4. washeluting with a gradient of 0 to 35% EtOAc in DCM

Sources & evidence

ORD record
ord-632fa112846e48f29b4e0c20a300ab5f
Source dataset
uspto-grants-2012_06
Patent number
US08207177B2

Reaction notes

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