Hydrochloric Acid → HCID 22484555, compound

HRID 398230

Reaction equation

HRID 398230 reaction equation
[H-].[Na+].[CH:3]1([OH:9])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[CH2:10]([N:17]1[C:21]2[N:22]=[CH:23][N:24]=[C:25](Cl)[C:20]=2[CH:19]=[CH:18]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.Cl>C1COCC1>[CH2:10]([N:17]1[C:21]2[N:22]=[CH:23][N:24]=[C:25]([O:9][CH:3]3[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]3)[C:20]=2[CH:19]=[CH:18]1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7966CyclohexanolHCID 24758Sodium hydrideHCID 151853564-Chloro-7-(phenylmethyl)-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 22484555HCID 22484555, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a flame dried flask under nitrogen was charged 84 mg (2.10 mmol) of 60% sodium hydride in mineral oil and 3.0 mL of THF and the mixture cooled to 0° C. Cyclohexanol (0.18 mL/1.70 mmol) was added and the reaction mixture stirred for 5 min. A solution of 102 mg (0.419 mmol) of the product from Method L in 1.0 mL of THF was added and the mixture heated to reflux for 3 h. After cooling to room temperature, the reaction mixture was acidified to pH 1 with 2 N HCl and concentrated in vacuo. The resulting residue was then slurried in ethyl acetate, filtered and the filtrate concentrated in vacuo to provide 76 mg (59%) of the title compound as an oil. LRMS: 308 (M+1).

Workup

  1. customTo a flame dried flask under nitrogen
  2. temperaturethe mixture heated
  3. temperatureto reflux for 3 h
  4. temperatureAfter cooling to room temperature
  5. concentrationconcentrated in vacuo
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-1af6729f32d649eb86ec7855e7a28507
Source dataset
uspto-grants-2003_08
Patent number
US06610847B2

Linked notes

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