Hydrochloric Acid → 6-(4-Amino-2-fluorophenoxy)-N-(4-(benzyloxy)phenyl)pyrimidin-4-amine

HRID 1670237Notes

Reaction equation

HRID 1670237 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]2[N:21]=[CH:20][N:19]=[C:18]([O:22][C:23]3[CH:28]=[CH:27][C:26]([NH:29]C(=O)C)=[CH:25][C:24]=3[F:33])[CH:17]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>CO>[NH2:29][C:26]1[CH:27]=[CH:28][C:23]([O:22][C:18]2[N:19]=[CH:20][N:21]=[C:16]([NH:15][C:12]3[CH:11]=[CH:10][C:9]([O:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[CH:14][CH:13]=3)[CH:17]=2)=[C:24]([F:33])[CH:25]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59852842N-(4-(6-(4-(benzyloxy)phenylamino)pyrimidin-4-yloxy)-3-fluorophenyl)acetamide

Product 1

HCID 598530036-(4-Amino-2-fluorophenoxy)-N-(4-(benzyloxy)phenyl)pyrimidin-4-amineYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of N-(4-(6-(4-(benzyloxy)phenylamino)pyrimidin-4-yloxy)-3-fluorophenyl)acetamide (150 mg, 0.34 mmol), 6 M HCl (0.5 mL) and MeOH (3 mL) was heated at reflux for 2 h. The mixture was concentrated to remove the MeOH and the residue treated with saturated NaHCO3 solution and extracted with EtOAc. The organic phase was dried (MgSO4) and concentrated in vacuo to give the title compound (123 mg, 90%) as a pink solid. 1H NMR (DMSO-d6): δ 9.37 (s, 1H), 8.24 (s, 1H), 7.46-7.31 (m, 7H), 6.99-6.92 (m, 3H), 6.48 (dd, 1H, J=12.5, 2.7 Hz), 6.39 (dd, 1H, J=8.6, 2.7 Hz), 5.97 (s, 1H), 5.39 (br s, 2H), 5.08 (s, 2H); MS (ESI+) m/z 403.09 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. concentrationThe mixture was concentrated
  4. customto remove the MeOH
  5. additionthe residue treated with saturated NaHCO3 solution
  6. extractionextracted with EtOAc
  7. dry with materialThe organic phase was dried (MgSO4)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8c668997d9624ed5afcf45d1d33888cb
Source dataset
uspto-grants-2011_08
Patent number
US07989477B2

Reaction notes

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