Hydrochloric Acid → HCID 22484482, compound

HRID 2180963Notes

Reaction equation

HRID 2180963 reaction equation
Cl[C:2]1[C:3]2[CH:10]=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[CH:11]1([SH:17])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.CC(C)([O-])C.[K+].Cl>C1COCC1>[CH: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)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 15290CyclohexanethiolHCID 53566827H-Pyrrolo(2,3-d)pyrimidine, 4-chloro-HCID 23665647Potassium tert-butoxide

Product 1

HCID 22484482HCID 22484482, compoundYield 22.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 100 mg (0.651 mmol) of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine dissolved in 3.0 mL of THF was added 0.10 mL (0.818 mmol) of cyclohexylmercaptan and 100 mg (0.847 mmol) of 95% potassium tert-butoxide and the resulting mixture heated at reflux for 3.5 hr. After cooling to room temperature, the reaction mixture was acidified to pH 1 with 2 N HCl and concentrated in vacuo. The residue was then partitioned between ethylacetate and 1 N HCl. The aqueous layer was extracted with ethyl acetate, the ethyl acetate layers were combined, washed with brine, dried over MgSO4, filtered, and evaporated in vacuo. The cude product was purified by silica-gel chromatography (1:3 ethylacetate/hexanes) providing 34 mg (22%) of the title compound as a white solid. Mp 162-163° C. 1H NMR (400 MHz) d: 1.22-1.36 (m, 1H), 1.45-1.64 (m, 5H), 1.75-1.79 (m, 2H), 2.12-2.14 (m, 2H), 4.18-4.20 (m, 1H), 6.50 (d, 1H, J=3.7 Hz), 7.19 (d, 1H, J=3.5 Hz), 8.61 (s, 1H), 10.0 (br s, 1H). LRMS: 234 (M+1).

Workup

  1. temperaturethe resulting mixture heated
  2. temperatureat reflux for 3.5 hr
  3. concentrationconcentrated in vacuo
  4. customThe residue was then partitioned between ethylacetate and 1 N HCl
  5. extractionThe aqueous layer was extracted with ethyl acetate
  6. washwashed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. customThe cude product was purified by silica-gel chromatography (1:3 ethylacetate/hexanes)

Sources & evidence

ORD record
ord-0c153b6b6ff14ab9ac3dafe4242f1a63
Source dataset
uspto-grants-2005_05
Patent number
US06890929B2

Reaction notes

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