Trifluoroacetic acid → {1-[(5-Chloro-2,4-dimethoxy-phenylcarbamoyl)-methyl]-2,4-dioxo-1,4-dihydro-2H-pyrido[3,2-d]pyrimidin-3-yl}-acetic acid

HRID 472738Notes

Reaction equation

HRID 472738 reaction equation
C([O:5][C:6](=[O:35])[CH2:7][N:8]1[C:13](=[O:14])[C:12]2[N:15]=[CH:16][CH:17]=[CH:18][C:11]=2[N:10]([CH2:19][C:20](=[O:33])[NH:21][C:22]2[CH:27]=[C:26]([Cl:28])[C:25]([O:29][CH3:30])=[CH:24][C:23]=2[O:31][CH3:32])[C:9]1=[O:34])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:28][C:26]1[C:25]([O:29][CH3:30])=[CH:24][C:23]([O:31][CH3:32])=[C:22]([NH:21][C:20]([CH2:19][N:10]2[C:11]3[CH:18]=[CH:17][CH:16]=[N:15][C:12]=3[C:13](=[O:14])[N:8]([CH2:7][C:6]([OH:35])=[O:5])[C:9]2=[O:34])=[O:33])[CH:27]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68589926{1-[(5-chloro-2,4-dimethoxy-phenylcarbamoyl)-methyl]-2,4-dioxo-1,4-dihydro-2H-pyrido[3,2-d]pyrimidin-3-yl}-acetic acid tert-butyl ester2×

Product 1

HCID 59317706{1-[(5-Chloro-2,4-dimethoxy-phenylcarbamoyl)-methyl]-2,4-dioxo-1,4-dihydro-2H-pyrido[3,2-d]pyrimidin-3-yl}-acetic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirring solution of {1-[(5-chloro-2,4-dimethoxy-phenylcarbamoyl)-methyl]-2,4-dioxo-1,4-dihydro-2H-pyrido[3,2-d]pyrimidin-3-yl}-acetic acid tert-butyl ester (Intermediate R) (22.1 mg, 0.044 mmol) in DCM (1 ml) is treated with TFA (1 ml). The reaction mixture is stirred at RT and monitored by HPLC/LCMS until the starting material is consumed. After 3 hours, the reaction mixture is diluted with a minimal amount of DCM and concentrated in vacuo. The residue is taken up in a minimal amount of MeOH, concentrated in vacuo, the again in a minimal amount of EtOAc and concentrated in vacuo to afford the title compound as an off white solid; [M+H]+ 449

Workup

  1. customis consumed
  2. additionthe reaction mixture is diluted with a minimal amount of DCM
  3. concentrationconcentrated in vacuo
  4. concentrationconcentrated in vacuo
  5. concentrationthe again in a minimal amount of EtOAc and concentrated in vacuo

Sources & evidence

ORD record
ord-7444cbe4352f474b8204fd53bf0d6fed
Source dataset
uspto-grants-2014_01
Patent number
US08633211B2

Reaction notes

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