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

HRID 1775185Notes

Reaction equation

HRID 1775185 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-4cb603b25407474895a78aba09d5563c
Source dataset
uspto-grants-2016_02
Patent number
US09260437B2

Reaction notes

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