Trifluoroacetic acid → HCID 73295448, compound

HRID 522959Notes

Reaction equation

HRID 522959 reaction equation
[C:1]([NH:5][C:6]([C:8]1[C:16]2[C:11](=[N:12][CH:13]=[C:14]([NH:17][C:18]3[CH:19]=[N:20][C:21]([CH3:24])=[N:22][CH:23]=3)[N:15]=2)[N:10](COCC[Si](C)(C)C)[CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].FC(F)(F)C(O)=O>ClCCl.CO.[OH-].[NH4+]>[C:1]([NH:5][C:6]([C:8]1[C:16]2[C:11](=[N:12][CH:13]=[C:14]([NH:17][C:18]3[CH:23]=[N:22][C:21]([CH3:24])=[N:20][CH:19]=3)[N:15]=2)[NH:10][CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131735550HCID 131735550, compound

Product 1

HCID 73295448HCID 73295448, compoundYield 77.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×HCID 14923Ammonium HydroxideSolvent

Procedure

To a solution of N-tert-butyl-2-(2-methylpyrimidin-5-ylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (78 mg, 171 μmol) in dichloromethane (2.5 mL) was added trifluoroacetic acid (390 mg, 264 μL, 3.42 mmol) and the mixture stirred at room temperature for 16 h. The reaction mixture was concentrated in vacuo and the residue obtained diluted with dichloromethane (2.5 mL), methanol (1.2 mL) and ammonium hydroxide (0.35 mL) and the mixture stirred at room temperature for 1 h. The reaction mixture was concentrated in vacuo then triturated with water. The solid was collected by filtration and washed with water and ether to give N-tert-butyl-2-(2-methylpyrimidin-5-ylamino)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (43 mg, 132 μmol, 77%) as a brown solid. 1H NMR (400 MHz, DMSO-d) δ ppm: 12.31 (s, 1H), 9.57 (s, 1H), 8.90 (s, 2H), 7.96 (d, J=3.3, 1H), 7.92 (s, 1H), 7.53 (s, 1H), 2.46 (s, 3H), 1.32 (s, 9H); MS (EI/CI) m/z: 326.1 [M+H].

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue obtained
  3. stirringthe mixture stirred at room temperature for 1 h
  4. concentrationThe reaction mixture was concentrated in vacuo
  5. customthen triturated with water
  6. filtrationThe solid was collected by filtration
  7. washwashed with water and ether

Sources & evidence

ORD record
ord-223d8e0e223648fe9c65a3f9ad790ecf
Source dataset
uspto-grants-2016_05
Patent number
US09334278B2

Reaction notes

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