Hydrochloric Acid → 3-methyl-4-(2-(methylamino)quinazolin-6-yl)-1,7-naphthyridin-8(7H)-one

HRID 2092339Notes

Reaction equation

HRID 2092339 reaction equation
COC1C=CC(C[N:8]2[C:17](=[O:18])[C:16]3[N:15]=[CH:14][C:13]([CH3:19])=[C:12]([C:20]4[CH:21]=[C:22]5[C:27](=[CH:28][CH:29]=4)[N:26]=[C:25]([NH:30][CH3:31])[N:24]=[CH:23]5)[C:11]=3[CH:10]=[CH:9]2)=CC=1.C(O)(C(F)(F)F)=O.Cl>>[CH3:19][C:13]1[CH:14]=[N:15][C:16]2[C:17](=[O:18])[NH:8][CH:9]=[CH:10][C:11]=2[C:12]=1[C:20]1[CH:21]=[C:22]2[C:27](=[CH:28][CH:29]=1)[N:26]=[C:25]([NH:30][CH3:31])[N:24]=[CH:23]2

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 58942251HCID 58942251, compound

Product 1

HCID 673399143-methyl-4-(2-(methylamino)quinazolin-6-yl)-1,7-naphthyridin-8(7H)-one

Conditions

Temperature
175 °C

Procedure

7-(4-Methoxybenzyl)-3-methyl-4-(2-(methylamino)quinazolin-6-yl)-1,7-naphthyridin-8(7H)-one (0.900 g, 2.06 mmol) was taken in a clear microwave vial and treated with 14 ml of TFA and 1 ml of cone HCl. The vial was capped and heated in a Personal Chemistry SmithSynthesizer to 175° C. for 45 minutes. The volatiles were evaporated under reduced pressure and residual TFA/water was azeotroped with toluene. The residue was taken up in DCM/2M MeOH and loaded unto silica. The residue was purified by column chromatography on silica gel using a gradient of 3 to 12% MeOH in DCM to give 3-methyl-4-(2-(methylamino)quinazolin-6-yl)-1,7-naphthyridin-8(7H)-one as a yellow solid. MS(M+H)+ 318.

Workup

  1. customThe vial was capped
  2. customThe volatiles were evaporated under reduced pressure and residual TFA/water
  3. customwas azeotroped with toluene
  4. customThe residue was purified by column chromatography on silica gel using a gradient of 3 to 12% MeOH in DCM

Sources & evidence

ORD record
ord-c1521836354848679f2f80d2bff41eaf
Source dataset
uspto-grants-2013_05
Patent number
US08440674B2

Reaction notes

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