Potassium Carbonate → 3-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-5-yl)benzonitrile

HRID 1750273Notes

Reaction equation

HRID 1750273 reaction equation
[Cl:1][C:2]1[C:3]2[C:10]([C:11]3[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=3)[C:14]#[N:15])=[CH:9][N:8](CO)[C:4]=2[N:5]=[CH:6][N:7]=1.C(=O)([O-])[O-].[K+].[K+]>CO>[Cl:1][C:2]1[C:3]2[C:10]([C:11]3[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=3)[C:14]#[N:15])=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 867069523-[4-chloro-7-(hydroxymethyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile

Product 1

HCID 867069533-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-5-yl)benzonitrile

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3-[4-chloro-7-(hydroxymethyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile (C13) (4 g from the previous step, ≦9.9 mmol) in methanol (100 mL) was adjusted to pH>12 by addition of solid potassium carbonate. Solvent was removed in vacuo and the residue was mixed with water (100 mL). The resulting solid was isolated via filtration and washed with water, providing the product as a white solid. Yield: 1.3 g, 5.1 mmol, 52% over two steps. LCMS m/z 255.0 [M+H+].

Workup

  1. customSolvent was removed in vacuo
  2. additionthe residue was mixed with water (100 mL)
  3. customThe resulting solid was isolated via filtration
  4. washwashed with water

Sources & evidence

ORD record
ord-bcebf8b53d9c434fa914b4837a4768b4
Source dataset
uspto-grants-2015_10
Patent number
US09156845B2

Reaction notes

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