Sodium Hydroxide → 3-(2-amino-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)benzoic acid

HRID 338676Notes

Reaction equation

HRID 338676 reaction equation
C([O:3][C:4](=[O:22])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N:11]2[CH2:21][CH2:20][C:14]3[N:15]=[C:16]([NH2:19])[N:17]=[CH:18][C:13]=3[CH2:12]2)[CH:6]=1)C.[OH-].[Na+]>O1CCOCC1>[NH2:19][C:16]1[N:17]=[CH:18][C:13]2[CH2:12][N:11]([C:7]3[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=3)[C:4]([OH:22])=[O:3])[CH2:21][CH2:20][C:14]=2[N:15]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86695814Ethyl-3-(2-amino-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-6-yl)-benzoate

Product 1

HCID 866958153-(2-amino-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)benzoic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A suspension of ethyl-3-(2-amino-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-6-yl)-benzoate (958 mg, 3.21 mmol) in 1,4-dioxane (35 mL) was treated with 1.0N NaOH(aq.) (8.24 mL, 8.24 mmol) and the reaction mixture was refluxed for 21 hours. Upon cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The residue was diluted with water and the pH was adjusted to ˜4 with 1.0N HCl(aq.). The cloudy mixture was treated with ethyl acetate and the aqueous/organic mixture was stirred at room temperature for approx. 1 hour. The precipitate was filtered off, washed with water, ethyl acetate, and dried in vacuo at 50° C. to give the title compound as a yellow, amorphous solid (710.8 mg, 82%).

Workup

  1. temperaturethe reaction mixture was refluxed for 21 hours
  2. filtrationthe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. additionThe residue was diluted with water
  5. additionThe cloudy mixture was treated with ethyl acetate
  6. filtrationThe precipitate was filtered off
  7. washwashed with water, ethyl acetate
  8. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-a4dc8b87aad24322b1812dc45a9243ce
Source dataset
uspto-grants-2014_11
Patent number
US08889870B2

Reaction notes

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