2-Naphthalenethiol → HCID 178418688, compound

HRID 491374Notes

Reaction equation

HRID 491374 reaction equation
[CH:1]1([C:4]2[CH:5]=[C:6]([NH:9][C:10]3[CH:15]=[C:14]([Cl:16])[N:13]=[C:12](Cl)[N:11]=3)[NH:7][N:8]=2)[CH2:3][CH2:2]1.[CH:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][C:19]=1[SH:28].C(N(CC)CC)C>C(O)(C)(C)C>[Cl:16][C:14]1[N:13]=[C:12]([S:28][C:19]2[CH:20]=[CH:21][C:22]3[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:18]=2)[N:11]=[C:10]([NH:9][C:6]2[NH:7][N:8]=[C:4]([CH:1]3[CH2:3][CH2:2]3)[CH:5]=2)[CH:15]=1

Participants

5

Reactant 3

HCID 70582-NaphthalenethiolHCID 8471TriethylamineHCID 178418938HCID 178418938, compound

Product 1

HCID 178418688HCID 178418688, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

To a solution of (5-cyclopropyl-2H-pyrazol-3-yl)-(2,6-dichloropyrimidin-4-yl)-amine (211 mg, 0.781 mmol) and 2-naphthalenethiol (125-mg, 0.781 mmol) in tert-butanol (5 mL) was added triethylamine (174 μL, 1.25 mmol) and the resulting mixture was heated at reflux for 15 hours. The reaction mixture was cooled to room temperature and partitioned between ethyl acetate and aqueous NaHCO3. The organic layer was washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by flash chromatography (SiO2, Hexane/AcOEt gradient) to afford (6-chloro-2-(naphthalen-2-ylsulfanyl)-pyrimidin-4-yl]-(5-cyclopropyl-2H-pyrazol-3-yl)-amine.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 15 hours
  3. custompartitioned between ethyl acetate and aqueous NaHCO3
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography (SiO2, Hexane/AcOEt gradient)

Sources & evidence

ORD record
ord-f023398d2d48451a99ba07f213c1f376
Source dataset
uspto-grants-2009_05
Patent number
US07531536B2

Reaction notes

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