Trifluoroacetic acid → N-tert-butyl-2-(2-methoxypyrimidin-5-ylamino)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

HRID 522995Notes

Reaction equation

HRID 522995 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]([O:24][CH3:25])=[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>[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]([O:24][CH3:25])=[N:22][CH:23]=3)[N:15]=2)[NH:10][CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90040888N-tert-butyl-2-(2-methoxypyrimidin-5-ylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

Product 1

HCID 73295947N-tert-butyl-2-(2-methoxypyrimidin-5-ylamino)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamideYield 88.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-tert-Butyl-2-(2-methoxypyrimidin-5-ylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (100 mg, 212 μmol) was dissolved in dichloromethane and treated with trifluoroacetic acid (484 mg, 327 μL, 4.24 mmol). The mixture was stirred at room temperature for 16 h. The mixture was concentrated then re-dissolved in dichloromethane (3 mL), methanol (1.5 mL) and ammonium hydroxide (0.45 mL) and the mixture stirred at room temperature for 1 h. The mixture was concentrated in vacuo then triturated with water and filtered. The solid obtained was washed with ether then dried to give N-tert-butyl-2-(2-methoxypyrimidin-5-ylamino)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (64 mg, 187 μmol, 88%) as a yellow solid. 1H NMR (400 MHz, DMSO-d) δ ppm: 12.35 (s, 1H), 9.48 (s, 1H), 8.86 (s, 2H), 8.01 (s, 1H), 7.97 (s, 1H), 7.63 (s, 1H), 3.88 (s, 3H), 1.38 (s, 9H); MS (EI/CI) m/z: 342.1 [M+H].

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionthen re-dissolved in dichloromethane (3 mL)
  3. stirringmethanol (1.5 mL) and ammonium hydroxide (0.45 mL) and the mixture stirred at room temperature for 1 h
  4. concentrationThe mixture was concentrated in vacuo
  5. customthen triturated with water
  6. filtrationfiltered
  7. customThe solid obtained
  8. washwas washed with ether
  9. customthen dried

Sources & evidence

ORD record
ord-d779bc75444e4f119d43bc3a113c58cb
Source dataset
uspto-grants-2016_05
Patent number
US09334278B2

Reaction notes

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