Sodium Hydroxide → 4-Methyl-3-[2-(methylsulfanyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-6-yl]benzoic Acid

HRID 1052051Notes

Reaction equation

HRID 1052051 reaction equation
C[O:2][C:3](=[O:23])[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[C:6]([N:11]2[CH2:22][CH2:21][C:14]3[N:15]=[C:16]([S:19][CH3:20])[N:17]=[CH:18][C:13]=3[CH2:12]2)[CH:5]=1.[OH-].[Na+]>O1CCOCC1>[CH3:10][C:7]1[CH:8]=[CH:9][C:4]([C:3]([OH:23])=[O:2])=[CH:5][C:6]=1[N:11]1[CH2:22][CH2:21][C:14]2[N:15]=[C:16]([S:19][CH3:20])[N:17]=[CH:18][C:13]=2[CH2:12]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86695858Methyl-4-methyl-3-[2-(methylsulfanyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-6-yl]benzoate

Product 1

HCID 897987874-Methyl-3-[2-(methylsulfanyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-6-yl]benzoic AcidYield 87%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A solution of methyl-4-methyl-3-[2-(methylsulfanyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-6-yl]benzoate (82 mg, 0.249 mmol) in 1,4-dioxane (5 ml) was treated with 1.0 N NaOH (aq.) (0.748 ml, 0.748 mmol) and the reaction mixture was heated at 100° C. for 15 hours. The solvent was removed in vacuo and the residue was taken up in water. The aqueous mixture was washed with EtOAc and acidified to pH˜2-3 with 1.0 N HCl (aq.). The white, amorphous precipitate which formed was collected, washed with water, and dried to give the title compound (67 mg, 87%).

Workup

  1. customThe solvent was removed in vacuo
  2. washThe aqueous mixture was washed with EtOAc
  3. customThe white, amorphous precipitate which formed
  4. customwas collected
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-2f4fbc948ace440f9095180b5d320971
Source dataset
uspto-grants-2016_07
Patent number
US09388176B2

Reaction notes

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