Hydrogen Bromide → HCID 86267409, compound

HRID 709988Notes

Reaction equation

HRID 709988 reaction equation
C[O:2][C:3]1[C:8]([C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]3[CH:21]=[CH:20][N:19]=[C:18]([C:22]4[CH:23]=[N:24][N:25]([CH3:27])[CH:26]=4)[CH:17]=3)=[C:11]([CH3:28])[N:10]=2)=[CH:7][N:6]=[C:5]([NH:29][CH3:30])[N:4]=1.Br>C(O)(=O)C>[CH3:28][C:11]1[N:10]=[C:9]([C:8]2[C:3](=[O:2])[NH:4][C:5]([NH:29][CH3:30])=[N:6][CH:7]=2)[CH:14]=[CH:13][C:12]=1[O:15][C:16]1[CH:21]=[CH:20][N:19]=[C:18]([C:22]2[CH:23]=[N:24][N:25]([CH3:27])[CH:26]=2)[CH:17]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 90416670HCID 90416670, compound

Product 1

HCID 86267409HCID 86267409, compoundYield 53.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 4-methoxy-N-methyl-5-(6-methyl-5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)pyrimidin-2-amine (0.10 g, 0.25 mmol) in acetic acid (5 mL) was treated with HBr (0.12 mL, 1.0 mmol) and heated at 90° C. for 4 h. The mixture was cooled to RT, quenched with ice water, treated with NaHCO3 and NaCl, and extracted with EtOAc (3×). The combined organics were dried over Na2SO4, concentrated to dryness, the resulting material treated with MeCN (3 mL) and the solid was collected via filtration to afford 5-(6-methyl-5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)-2-(methylamino)pyrimidin-4(3H)-one (52 mg, 53%). 1H NMR (400 MHz, DMSO-d6): δ 11.26 (s, 1H), 8.70 (s, 1H), 8.36 (d, J=5.7 Hz, 1H), 8.28 (m, 1H), 8.26 (s, 1H), 7.97 (s, 1H), 7.51 (d, J=8.6 Hz, 1H), 7.22 (d, J=2.4 Hz, 1H), 6.70 (br s, 1H), 6.61 (dd, J=5.7, 2.4 Hz, 1H), 3.85 (s, 3H), 2.85 (d, J=4.7 Hz, 3H), 2.35 (s, 3H); MS (ESI) m/z: 390.2 (M+H+).

Workup

  1. temperatureThe mixture was cooled to RT
  2. customquenched with ice water
  3. additiontreated with NaHCO3 and NaCl
  4. extractionextracted with EtOAc (3×)
  5. dry with materialThe combined organics were dried over Na2SO4
  6. concentrationconcentrated to dryness
  7. additionthe resulting material treated with MeCN (3 mL)
  8. filtrationthe solid was collected via filtration

Sources & evidence

ORD record
ord-25ccce6cccbd4fe8aba6390b2a124e45
Source dataset
uspto-grants-2015_11
Patent number
US09181223B2

Reaction notes

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