Trifluoroacetic acid → HCID 60207822, compound

HRID 910261Notes

Reaction equation

HRID 910261 reaction equation
[CH2:1]([C:5]1[N:9]([C:10]2[N:15]=[C:14]([C:16]3[S:17][CH:18]=[CH:19][CH:20]=3)[C:13]([CH3:21])=[CH:12][N:11]=2)[N:8]=[CH:7][C:6]=1[NH:22]C(=O)OC(C)(C)C)[CH2:2][CH2:3][CH3:4].FC(F)(F)C(O)=O>C(Cl)(Cl)Cl>[CH2:1]([C:5]1[N:9]([C:10]2[N:15]=[C:14]([C:16]3[S:17][CH:18]=[CH:19][CH:20]=3)[C:13]([CH3:21])=[CH:12][N:11]=2)[N:8]=[CH:7][C:6]=1[NH2:22])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 60207821HCID 60207821, compound

Product 1

HCID 60207822HCID 60207822, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
23 °C

Procedure

To the solution of tert-butyl 5-butyl-1-(5-methyl-4-(thiophen-2-yl)pyrimidin-2-yl)-1H-pyrazol-4-ylcarbamate from step 1 in CHCl3 (30 mL) cooled to 0° C. was injected trifluoroacetic acid (3 mL) and let stir for 23 h at 23° C. The reaction solvent was then evaporated and redissolved in CH2Cl2 and washed with saturated NaHCO3 solution. The organic layer dried (sodium sulfate) and concentrated, whereupon the residue was purified by silica gel flash column chromatography (gradient from 2% methanol in dichloromethane to 10% methanol in dichloromethane) afford 5-butyl-1-(5-methyl-4-(thiophen-2-yl)pyrimidin-2-yl)-1H-pyrazol-4-amine (361 mg, 38% yield over 3 steps) as a yellow oil. 1H NMR (500 MHz, DMSO) δ 8.55 (s, 1H), 7.83 (dd, J=3.91, 0.98 Hz, 1H), 7.69 (dd, J=5.38, 0.98 Hz, 1H), 7.46 (s, 1H), 7.21 (dd, J=4.89, 3.91 Hz, 1H), 4.86 (bs, 2H), 3.19 (t, J=7.82 Hz, 2H), 2.53 (s, 3H), 4.53 (m, 2H), 1.36 (sex, J=7.83 Hz, 2H), 0.84 (t, J=7.34 Hz, 3H). LCMS (ES+) m/z 314 (M+1).

Workup

  1. customThe reaction solvent was then evaporated
  2. dissolutionredissolved in CH2Cl2
  3. washwashed with saturated NaHCO3 solution
  4. dry with materialThe organic layer dried (sodium sulfate)
  5. concentrationconcentrated, whereupon the residue
  6. customwas purified by silica gel flash column chromatography (gradient from 2% methanol in dichloromethane to 10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-1baf6ceef2a7489593fe3ae04703c233
Source dataset
uspto-grants-2011_09
Patent number
US08022061B2

Reaction notes

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