Cyclohexanol → HCID 59446942, compound

HRID 1746711Notes

Reaction equation

HRID 1746711 reaction equation
[CH:1]1([OH:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].Cl[C:11]1[N:16]=[CH:15][N:14]=[C:13]([C:17]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][C:21]=2C)=[O:18])[CH:12]=1>O1CCCC1>[CH:1]1([O:7][C:11]2[N:16]=[CH:15][N:14]=[C:13]([C:17]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=3)=[O:18])[CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 7966CyclohexanolHCID 24758Sodium hydrideHCID 594471056-chloro-N-(4-hydroxy-2-methylphenyl)pyrimidine-4-carboxamide2×

Product 1

HCID 59446942HCID 59446942, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Cyclohexanol (Fluka, 4.00 mL; 37.8 mmol) was treated with sodium hydride (35.0 mg; 0.80 mmol) and stirred during 10 minutes. Tetrahydrofuran (3 mL) was added, followed by 6-chloro-N-(4-hydroxy-2-methylphenyl)pyrimidine-4-carboxamide, Intermediate 7 (50.0 mg; 0.20 mmol). After 2 hours the solvents were removed in vacuo, the crude was redissolved in EtOAc. The organic phase was washed with sat. ammonium chloride and brine, dried over magnesium sulfate, filtered and evaporated in vacuo to give a residue, which was purified by column chromatography (silica) eluting with cyclohexane containing increasing amounts of EtOAc. The title compound was obtained as a white solid.

Workup

  1. customAfter 2 hours the solvents were removed in vacuo
  2. dissolutionthe crude was redissolved in EtOAc
  3. washThe organic phase was washed with sat. ammonium chloride and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customto give a residue, which
  8. customwas purified by column chromatography (silica)
  9. washeluting with cyclohexane containing
  10. temperatureincreasing amounts of EtOAc

Sources & evidence

ORD record
ord-72cbbba4a96c449dbb90cb630202e64d
Source dataset
uspto-grants-2015_10
Patent number
US09150519B2

Reaction notes

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