Trifluoroacetic acid → 5-(5-(1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-7-yl)-2-methylthiazole

HRID 1853028Notes

Reaction equation

HRID 1853028 reaction equation
[CH3:1][C:2]1[S:3][C:4]([C:7]2[N:12]=[C:11]([C:13]3[CH:14]=[N:15][N:16](COCC[Si](C)(C)C)[CH:17]=3)[N:10]3[CH:26]=[CH:27][N:28]=[C:9]3[CH:8]=2)=[CH:5][N:6]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:15]1[CH:14]=[C:13]([C:11]2[N:10]3[CH:26]=[CH:27][N:28]=[C:9]3[CH:8]=[C:7]([C:4]3[S:3][C:2]([CH3:1])=[N:6][CH:5]=3)[N:12]=2)[CH:17]=[N:16]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 866853182-methyl-5-(5-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-7-yl)thiazole

Product 1

HCID 674576205-(5-(1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-7-yl)-2-methylthiazoleYield 64.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-methyl-5-(5-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-7-yl)thiazole (0.196 g, 0.475 mmol) was dissolved in 3 mL of DCM before TFA (2.0 mL, 26.0 mmol) was added slowly at room temperature. The reaction was allowed to stir at room temperature for 8 hours. The reaction mixture was concentrated under reduced pressure to afford the crude material. The crude material was purified via column chromatography, eluting with 5% MeOH in DCM with 1% NH4OH to afford the title compound (0.087 g, 64.9% yield). MS (apci) m/z=283.1 (M+H).

Workup

  1. additionwas added slowly at room temperature
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customto afford the crude material
  4. customThe crude material was purified via column chromatography
  5. washeluting with 5% MeOH in DCM with 1% NH4OH

Sources & evidence

ORD record
ord-833ffec0fde441e7a3776a9f1b699705
Source dataset
uspto-grants-2015_02
Patent number
US08962596B2

Reaction notes

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