Trifluoroacetic acid → 6-fluoro-5-(7H-pyrrolo[2,3-d]pyrimidin-5-ylmethyl)-pyridin-2-ylamine

HRID 1403281Notes

Reaction equation

HRID 1403281 reaction equation
[F:1][C:2]1[N:7]=[C:6]([NH:8]CC2C=CC(OC)=CC=2)[CH:5]=[CH:4][C:3]=1[CH2:18][C:19]1[C:27]2[CH:26]=[N:25][CH:24]=[N:23][C:22]=2[NH:21][CH:20]=1.FC(F)(F)C(O)=O>ClCCl>[F:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[CH2:18][C:19]1[C:27]2[CH:26]=[N:25][CH:24]=[N:23][C:22]=2[NH:21][CH:20]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57963085[6-Fluoro-5-(7H-pyrrolo[2,3-d]pyrimidin-5-ylmethyl)-pyridin-2-yl]-(4-methoxy-benzyl)-amine

Product 1

HCID 579630566-fluoro-5-(7H-pyrrolo[2,3-d]pyrimidin-5-ylmethyl)-pyridin-2-ylamineYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To [6-fluoro-5-(7H-pyrrolo[2,3-d]pyrimidin-5-ylmethyl)-pyridin-2-yl]-(4-methoxy-benzyl)-amine (P-0105, 4.5 g, 12.38 mmol) in 100 mL of dichloromethane, trifluoroacetic acid (95 mL, 1.238 mol) was added. The reaction was stirred at reflux for several hours, then concentrated under vacuum. The resulting material was taken up in ethyl acetate and poured into aqueous potassium carbonate. The resulting solid was filtered, washed with water, azeotroped from toluene and triturated with dichloromethane. The solid was isolated by filtration to provide the desired compound as a white solid (68, 2.8 g, 11.51 mmol, 93% yield).

Workup

  1. temperatureat reflux for several hours
  2. concentrationconcentrated under vacuum
  3. additionpoured into aqueous potassium carbonate
  4. filtrationThe resulting solid was filtered
  5. washwashed with water
  6. customazeotroped from toluene
  7. customtriturated with dichloromethane
  8. customThe solid was isolated by filtration

Sources & evidence

ORD record
ord-8485352bfc3c4c61acf863b2847eb62d
Source dataset
uspto-grants-2014_12
Patent number
US08912204B2

Reaction notes

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