Trifluoroacetic acid → 4-(4-Aminonaphthalen-1-yloxy)pyrimidin-2-amine

HRID 2069151Notes

Reaction equation

HRID 2069151 reaction equation
C(OC([NH:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([O:19][C:20]2[CH:25]=[CH:24][N:23]=[C:22]([NH:26]C(=O)OC(C)(C)C)[N:21]=2)=[CH:11][CH:10]=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([O:19][C:20]2[CH:25]=[CH:24][N:23]=[C:22]([NH2:26])[N:21]=2)=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68322851tert-Butyl 4-(4-(tert-butoxycarbonylamino)naphthalen-1-yloxy)pyrimidin-2-ylcarbamate

Product 1

HCID 207688484-(4-Aminonaphthalen-1-yloxy)pyrimidin-2-amineYield 97.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-(4-(tert-butoxycarbonylamino)naphthalen-1-yloxy)pyrimidin-2-ylcarbamate (1.35 g, 2.98 mmol) in DCM (15 mL) was added TFA (5.0 mL) and the reaction mixture was set aside at RT for 3 hr. The mixture was evaporated in vacuo and the residue was taken up into EtOAc (25 mL) and washed with saturated NaHCO3 solution (25 mL) and brine (25 mL) and then dried (MgSO4) Evaporation in vacuo afforded the title compound as a beige solid (735 mg, 96%); Rt 0.98 min (Method 2); m/z 253 (M+H)+, (ES+)+.

Workup

  1. customThe mixture was evaporated in vacuo
  2. washwashed with saturated NaHCO3 solution (25 mL) and brine (25 mL)
  3. customdried
  4. custom(MgSO4) Evaporation in vacuo

Sources & evidence

ORD record
ord-921f54273e8f4f77b79b15f38f744f2a
Source dataset
uspto-grants-2012_10
Patent number
US08299074B2

Reaction notes

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