Tert-butyl 4-(2-(4-methoxybenzylamino)pyrimidin-4-yloxy)naphthalen-1-ylcarbamate → 4-(4-Aminonaphthalen-1-yloxy)pyrimidin-2-amine

HRID 2069154Notes

Reaction equation

HRID 2069154 reaction equation
COC1C=CC(C[NH:8][C:9]2[N:14]=[C:13]([O:15][C:16]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[C:19]([NH:26]C(=O)OC(C)(C)C)=[CH:18][CH:17]=3)[CH:12]=[CH:11][N:10]=2)=CC=1>C(O)(C(F)(F)F)=O>[NH2:26][C:19]1[C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:16]([O:15][C:13]2[CH:12]=[CH:11][N:10]=[C:9]([NH2:8])[N:14]=2)=[CH:17][CH:18]=1

Participants

3

Reactant 1

HCID 68322850Tert-butyl 4-(2-(4-methoxybenzylamino)pyrimidin-4-yloxy)naphthalen-1-ylcarbamate

Product 1

HCID 207688484-(4-Aminonaphthalen-1-yloxy)pyrimidin-2-amineYield 54%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of impure tert-butyl 4-(2-(4-methoxybenzylamino)pyrimidin-4-yloxy)naphthalen-1-ylcarbamate described above (0.77 g, ˜50% purity, 0.8 mmol) in TFA (10 mL) was heated at reflux for 8 hr and then kept at RT for 16 hr. The reaction mixture was evaporated in vacuo and the residue was taken up into EtOAc and was washed with saturated aq NaHCO3 solution and with brine and then dried (MgSO4) and evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, ethyl acetate in isohexane, 50-100%, gradient elution) to afford the title compound (111 mg, 54%) as a brown solid; m/z 253 (M+H)+, (ES+)+

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 8 hr
  3. customThe reaction mixture was evaporated in vacuo
  4. washwas washed with saturated aq NaHCO3 solution and with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated in vacuo
  7. customThe residue was purified by flash column chromatography (SiO2, ethyl acetate in isohexane, 50-100%, gradient elution)

Sources & evidence

ORD record
ord-0ae475d37e7447f3a689b4729d60fccc
Source dataset
uspto-grants-2012_10
Patent number
US08299074B2

Reaction notes

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