Trifluoroacetic acid → 5-(4-Phenoxy-phenyl)-7-pyrrolidin-3-yl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine

HRID 51528Notes

Reaction equation

HRID 51528 reaction equation
[NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([O:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:13][CH:12]=3)=[CH:9][N:8]([CH:24]3[CH2:28][CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25]3)[C:4]=2[N:5]=[CH:6][N:7]=1.FC(F)(F)C(O)=O>ClCCl>[O:17]([C:14]1[CH:13]=[CH:12][C:11]([C:10]2[C:3]3[C:2]([NH2:1])=[N:7][CH:6]=[N:5][C:4]=3[N:8]([CH:24]3[CH2:28][CH2:27][NH:26][CH2:25]3)[CH:9]=2)=[CH:16][CH:15]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22736315HCID 22736315, compound

Product 1

HCID 101383765-(4-Phenoxy-phenyl)-7-pyrrolidin-3-yl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamineYield 79.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 3-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]-1-pyrrolidinecarboxylate (0.8 g, 1.7 mmol) in dichloromethane (25 ml) at 0° C. was added trifluoroacetic acid (5 ml). The reaction mixture was warmed to room temperature and stirred at room temperature for 20 hr. The solvent was evaporated and dilute NaOH added (5N, 10 ml). The resulting residue solution was extracted with EtOAc (3×50 ml) and the combined organics were washed with brine (1×75 ml). The organic solution was dried (sodium sulphate), filtered and evaporated in vacuo to leave 5-(4-phenoxyphenyl)-7-(3-pyrrolidinyl) -7H-pyrrolo[2,3-d]pyrimidin-4-ylamine as a white solid (0.5 g, 79%) m.pt. 182-184° C. Rf in 1:1 EtOAc : MeOH=0.15. 1H NMR (d6 DMSO, 250 MHz): 8.14 (1H, s), 7.37-7.50 (5H, m), 7.05-7.18 (5H, m), 6.14 (2H, bs), 5.23 (1H, m), 3.09-3.27 (2H, m), 2.83-2.98 (2H, m), 2.19-2.33 (1H, m), 1.88-2.01 (1H, m). Mass spec. 371.1758 (C22H2 ON5). IR (KBr disc): 3106, 1585, 1489, 1232 cm−1.

Workup

  1. customThe solvent was evaporated
  2. additiondilute NaOH added (5N, 10 ml)
  3. extractionThe resulting residue solution was extracted with EtOAc (3×50 ml)
  4. washthe combined organics were washed with brine (1×75 ml)
  5. dry with materialThe organic solution was dried (sodium sulphate)
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-935451d393e54ad2be5d21533a6a4433
Source dataset
uspto-grants-2004_03
Patent number
US06713474B2

Reaction notes

Loading…