Hydrogen Bromide → HCID 86268026, compound

HRID 710002Notes

Reaction equation

HRID 710002 reaction equation
[CH2:1]([N:3]1[CH:7]=[C:6]([C:8]2[CH:13]=[C:12]([O:14][C:15]3[CH:16]=[CH:17][C:18]([C:22]4[C:23]([O:32]C)=[N:24][C:25]([NH:28][CH:29]([CH3:31])[CH3:30])=[N:26][CH:27]=4)=[N:19][C:20]=3[CH3:21])[CH:11]=[CH:10][N:9]=2)[CH:5]=[N:4]1)[CH3:2].Br>CC(O)=O>[CH2:1]([N:3]1[CH:7]=[C:6]([C:8]2[CH:13]=[C:12]([O:14][C:15]3[CH:16]=[CH:17][C:18]([C:22]4[C:23](=[O:32])[NH:24][C:25]([NH:28][CH:29]([CH3:31])[CH3:30])=[N:26][CH:27]=4)=[N:19][C:20]=3[CH3:21])[CH:11]=[CH:10][N:9]=2)[CH:5]=[N:4]1)[CH3:2]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 90417737HCID 90417737, compound

Product 1

HCID 86268026HCID 86268026, compoundYield 76.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

5-(5-((2-(1-ethyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)-6-methylpyridin-2-yl)-N-isopropyl-4-methoxypyrimidin-2-amine (0.25 g, 0.56 mmol) was dissolved in AcOH (5 mL) and 48% hydrobromic acid (0.25 mL, 2.24 mmol) was added. The mixture was heated at 90° C. for 5 hours. The mixture was evaporated under high vacuum. The residue was treated with NaHCO3 solution and the solution was extracted with EtOAc (3×). The organic was dried over Na2SO4, filtered, and concentrated. The residue was treated with hot MeCN. The solid was filtered, and dried under vacuum to obtain 5-(5-((2-(1-ethyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)-6-methylpyridin-2-yl)-2-(isopropylamino)pyrimidin-4(3H)-one (185 mg, 73.1% yield). 1H NMR (400 MHz, DMSO-d6): δ 10.81 (s, 1H), 8.68 (s, 1H), 8.36 (d, J=5.7 Hz, 1H), 8.31 (s, 1H), 8.26 (d, J=8.6 Hz, 1H), 7.98 (s, 1H), 7.51 (d, J=8.6 Hz, 1H), 7.24 (d, J=2.4 Hz, 1H), 6.60 (dd, J=5.7, 2.4 Hz, 1H), 4.14 (q, J=7.3 Hz, 2H), 4.07 (m, 1H), 2.34 (s, 3H), 1.37 (t, J=7.3 Hz, 3H), 1.17 (d, J=6.5 Hz, 6H); MS (ESI) m/z: 432.2 (M+H+).

Workup

  1. customThe mixture was evaporated under high vacuum
  2. additionThe residue was treated with NaHCO3 solution
  3. extractionthe solution was extracted with EtOAc (3×)
  4. dry with materialThe organic was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. additionThe residue was treated with hot MeCN
  8. filtrationThe solid was filtered
  9. customdried under vacuum

Sources & evidence

ORD record
ord-6d9fa83908e747f5a4fa5203ef9544fe
Source dataset
uspto-grants-2015_11
Patent number
US09181223B2

Reaction notes

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