Trifluoroacetic acid → 4-(5-fluoro-2-methoxyphenyl)-6-(1,2,3,6-tetrahydropyridin-4-yl)-7H-pyrrolo[2,3-d]pyrimidine

HRID 527996Notes

Reaction equation

HRID 527996 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:30][CH3:31])=[C:6]([C:8]2[C:9]3[CH:16]=[C:15]([C:17]4[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH:18]=4)[NH:14][C:10]=3[N:11]=[CH:12][N:13]=2)[CH:7]=1.FC(F)(F)C(O)=O>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:30][CH3:31])=[C:6]([C:8]2[C:9]3[CH:16]=[C:15]([C:17]4[CH2:22][CH2:21][NH:20][CH2:19][CH:18]=4)[NH:14][C:10]=3[N:11]=[CH:12][N:13]=2)[CH:7]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90418673tert-butyl 4-(4-(5-fluoro-2-methoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-5,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 784258544-(5-fluoro-2-methoxyphenyl)-6-(1,2,3,6-tetrahydropyridin-4-yl)-7H-pyrrolo[2,3-d]pyrimidine

Procedure

To a solution of Example 3E (900 mg, 2.120 mmol) in 10 mL dicholoromethane was added trifluoroacetic acid (1.634 mL, 21.2 mmol). The mixture was stirred at room temperature for 2 hours and the solvent was removed by azeotroping with ethyl acetate. The residue was dissolved in 3 mL methanol and treated with 2M hydrogen chloride in ether (1 mL) for 1 hour. The mixture was diluted with ether and the solid filtered to give the title compound as a hydrochloride salt. 1H NMR (300 MHz, DMSO-d6) δ 2.64-2.81 (m, 2H) 3.76-3.82 (m, 3H) 3.81-3.90 (m, 2H) 6.52 (s, 1H) 6.56 (s, 1H) 7.17-7.33 (m, 1H) 7.32-7.49 (m, 2H) 8.86 (s, 1H) 8.95 (s, 2H) 12.57 (s, 1H). MS (ESI+) m/z 325.1 (M+H)+.

Workup

  1. customthe solvent was removed
  2. customby azeotroping with ethyl acetate
  3. dissolutionThe residue was dissolved in 3 mL methanol
  4. additiontreated with 2M hydrogen chloride in ether (1 mL) for 1 hour
  5. additionThe mixture was diluted with ether
  6. filtrationthe solid filtered

Sources & evidence

ORD record
ord-c4f04c4b574245be94b2a6037ac4c673
Source dataset
uspto-grants-2016_05
Patent number
US09346813B2

Reaction notes

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