Hydrogen Bromide → HCID 86270438, compound

HRID 709979Notes

Reaction equation

HRID 709979 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]([N:29]([CH3:31])[CH3:30])[N:4]=1.Br>C(O)(=O)C>[CH3:30][N:29]([CH3:31])[C:5]1[NH:4][C:3](=[O:2])[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]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 90416418HCID 90416418, compound

Product 1

HCID 86270438HCID 86270438, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 4-methoxy-N,N-dimethyl-5-(6-methyl-5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)pyrimidin-2-amine (0.060 g, 0.144 mmol) in acetic acid (5 mL) was treated with HBr (0.065 mL, 0.575 mmol), heated at 90° C. for 6 h, cooled to RT and quenched with ice water. The solution was treated with NaHCO3 and NaCl, extracted with 1:1 THF/EtOAc (3×) and the combined organics were dried over Na2SO4 and concentrated to dryness. The material was treated with MeCN (1 mL), allowed to stand at RT and the resulting solid was collected via filtration to afford 2-(dimethylamino)-5-(6-methyl-5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)pyrimidin-4(3H)-one (43 mg, 71%). 1H NMR (400 MHz, DMSO-d6): δ 11.23 (s, 1H), 8.73 (s, 1H), 8.36 (d, J=5.7 Hz, 1H), 8.30 (m, 1H), 8.26 (s, 1H), 7.97 (s, 1H), 7.51 (m, 1H), 7.23 (d, J=2.4 Hz, 1H), 6.62 (br s, 1H), 3.85 (s, 3H), 3.12 (s, 6H), 2.35 (s, 3H); MS (ESI) m/z: 404.2 (M+H+).

Workup

  1. temperaturecooled to RT
  2. customquenched with ice water
  3. additionThe solution was treated with NaHCO3 and NaCl
  4. extractionextracted with 1:1 THF/EtOAc (3×)
  5. dry with materialthe combined organics were dried over Na2SO4
  6. concentrationconcentrated to dryness
  7. additionThe material was treated with MeCN (1 mL)
  8. customto stand at RT
  9. filtrationthe resulting solid was collected via filtration

Sources & evidence

ORD record
ord-6214efa98e9c4a3586d6641005c54df9
Source dataset
uspto-grants-2015_11
Patent number
US09181223B2

Reaction notes

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