Trifluoroacetic acid → 3-(2-aminoquinazolin-6-yl)-4-methylpyridin-2(1H)-one

HRID 643515Notes

Reaction equation

HRID 643515 reaction equation
COC1C=CC(C[O:8][C:9]2[C:14]([C:15]3[CH:16]=[C:17]4[C:22](=[CH:23][CH:24]=3)[N:21]=[C:20]([NH2:25])[N:19]=[CH:18]4)=[C:13]([CH3:26])[CH:12]=[CH:11][N:10]=2)=CC=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:25][C:20]1[N:19]=[CH:18][C:17]2[C:22](=[CH:23][CH:24]=[C:15]([C:14]3[C:9](=[O:8])[NH:10][CH:11]=[CH:12][C:13]=3[CH3:26])[CH:16]=2)[N:21]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 669999546-(2-(4-Methoxybenzyloxy)-4-methylpyridin-3-yl)quinazolin-2-amine

Product 1

HCID 669999863-(2-aminoquinazolin-6-yl)-4-methylpyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-(2-(4-methoxybenzyloxy)-4-methylpyridin-3-yl)quinazolin-2-amine (0.650 g, 1.75 mmol) in CH2Cl2 (1 mL) at RT was added TFA (1.00 ml, 13.0 mmol). After 10 min the solvent and excess acid was removed in vacuo. The residue was taken up in EtOAc and saturated NaHCO3 was added. The resulting white precipitate was removed by filtration. The solid material, 3-(2-aminoquinazolin-6-yl)-4-methylpyridin-2(1H)-one, was dried in vacuo and used without further purification. M+H+=253.1.

Workup

  1. customAfter 10 min the solvent and excess acid was removed in vacuo
  2. additionsaturated NaHCO3 was added
  3. customThe resulting white precipitate was removed by filtration
  4. dry with materialThe solid material, 3-(2-aminoquinazolin-6-yl)-4-methylpyridin-2(1H)-one, was dried in vacuo
  5. customused without further purification

Sources & evidence

ORD record
ord-0d8914f2cf8d43c8b183bae78f2f85bf
Source dataset
uspto-grants-2010_04
Patent number
US07700607B2

Reaction notes

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