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

HRID 2373984Notes

Reaction equation

HRID 2373984 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-429316ec08354c609983ef8e94bd82de
Source dataset
uspto-grants-2008_12
Patent number
US07459562B2

Reaction notes

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