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

HRID 472740Notes

Reaction equation

HRID 472740 reaction equation
C([O:5][C:6](=[O:35])[CH2:7][N:8]1[C:13](=[O:14])[C:12]2[CH:15]=[CH:16][N: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(Cl)Cl.C(O)(C(F)(F)F)=O>[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]=[N:17][CH:16]=[CH: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 1

HCID 68591872{1-[(5-Chloro-2,4-dimethoxy-phenylcarbamoyl)-methyl]-2,4-dioxo-1,4-dihydro-2H-pyrido[3,4-d]pyrimidin-3-yl}-acetic acid tert-butyl ester2×

Product 1

HCID 59317715{1-[(5-Chloro-2,4-dimethoxy-phenylcarbamoyl)-methyl]-2,4-dioxo-1,4-dihydro-2H-pyrido[3,4-d]pyrimidin-3-yl}-acetic acid

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 6422Trifluoroacetic acidSolvent

Procedure

To a vial containing a solution of {1-[(5-Chloro-2,4-dimethoxy-phenylcarbamoyl)-methyl]-2,4-dioxo-1,4-dihydro-2H-pyrido[3,4-d]pyrimidin-3-yl}-acetic acid tert-butyl ester (Intermediate V) (15 mg, 0.029 mmol) in DCM (1 ml), TFA (1 ml) is added. The mixture is stirred at RT overnight. The reaction mixture is then transferred to a 10 ml round bottomed flask, diluted with a minimal amount of DCM and concentrated in vacuo. This process is repeated once with DCM, twice with EtOAc, and once with MeOH, the solvent being concentrated in vacuo each time, finally giving the title, [M+H]+ 448.93.

Workup

  1. additionis added
  2. customThe reaction mixture is then transferred to a 10 ml round bottomed flask
  3. concentrationconcentrated in vacuo
  4. concentrationonce with MeOH, the solvent being concentrated in vacuo each time
  5. customfinally giving the title, [M+H]+ 448.93

Sources & evidence

ORD record
ord-df3b5711aed44185807392589d886346
Source dataset
uspto-grants-2014_01
Patent number
US08633211B2

Reaction notes

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