Hydrochloric Acid → [1-(1,4-dimethyl-1H-indol-3-ylmethyl)-2,4-dioxo-1,4-dihydro-2H-pyrido[3,4-d]pyrimidin-3-yl]-acetic acid

HRID 1887190Notes

Reaction equation

HRID 1887190 reaction equation
C[O:2][C:3](=[O:29])[CH2:4][N:5]1[C:10](=[O:11])[C:9]2[CH:12]=[CH:13][N:14]=[CH:15][C:8]=2[N:7]([CH2:16][C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][C:24]=3[CH3:26])[N:19]([CH3:27])[CH:18]=2)[C:6]1=[O:28].[OH-].[Li+].Cl.O>O1CCOCC1>[CH3:27][N:19]1[C:20]2[C:25](=[C:24]([CH3:26])[CH:23]=[CH:22][CH:21]=2)[C:17]([CH2:16][N:7]2[C:8]3[CH:15]=[N:14][CH:13]=[CH:12][C:9]=3[C:10](=[O:11])[N:5]([CH2:4][C:3]([OH:29])=[O:2])[C:6]2=[O:28])=[CH:18]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 67502958[1-(1,4-dimethyl-1H-indol-3-ylmethyl)-2,4-dioxo-1,4-dihydro-2H-pyrido[3,4-d]pyrimidin-3-yl]-acetic acid methyl ester

Product 1

HCID 46853638[1-(1,4-dimethyl-1H-indol-3-ylmethyl)-2,4-dioxo-1,4-dihydro-2H-pyrido[3,4-d]pyrimidin-3-yl]-acetic acidYield 67%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 70 mg of [1-(1,4-dimethyl-1H-indol-3-ylmethyl)-2,4-dioxo-1,4-dihydro-2H-pyrido[3,4-d]pyrimidin-3-yl]-acetic acid methyl ester in 1,4-dioxane (2.0 mL) is added lithium hydroxide solution (11 mg of lithium hydroxide monohydrate in 0.5 mL of water) at room temperature. The solution is stirred at the same temperature for 5 h. Then 1.0 mL of 1.0 M hydrochloric acid is added along with 50 mL of water. The mixture is extracted with ethyl acetate (3×50 mL) and the organic layers are combined, dried over magnesium sulfate and concentrated to give crude product. The crude product is rinsed with methanol (3.0 mL) and dichloromethane (5.0 mL) and the remaining light yellow solid is dried to give 45 mg (67%) of [1-(1,4-dimethyl-1H-indol-3-ylmethyl)-2,4-dioxo-1,4-dihydro-2H-pyrido[3,4-d]pyrimidin-3-yl]-acetic acid; LCMS (ESMS): m/z 379.16 (M+H+).

Workup

  1. extractionThe mixture is extracted with ethyl acetate (3×50 mL)
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. customto give crude product
  5. washThe crude product is rinsed with methanol (3.0 mL) and dichloromethane (5.0 mL)
  6. customthe remaining light yellow solid is dried

Sources & evidence

ORD record
ord-3e31de601a954818b8115c48278db403
Source dataset
uspto-grants-2013_08
Patent number
US08501749B2

Reaction notes

Loading…