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

HRID 558462Notes

Reaction equation

HRID 558462 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-a8d80a3b7f534a598158b134a29665e3
Source dataset
uspto-grants-2011_11
Patent number
US08063055B2

Reaction notes

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