Sodium Hydroxide → 6-[2-(Methylthio)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-6-yl]pyridine-2-carboxylic acid

HRID 1052019Notes

Reaction equation

HRID 1052019 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([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)[N:6]=1)=[O:4].[OH-].[Na+]>O1CCOCC1>[CH3:20][S:19][C:16]1[N:17]=[CH:18][C:13]2[CH2:12][N:11]([C:7]3[N:6]=[C:5]([C:3]([OH:4])=[O:2])[CH:10]=[CH:9][CH:8]=3)[CH2:22][CH2:21][C:14]=2[N:15]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86695834Methyl-6-[2-(methylthio)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-6-yl]pyridine-2-carboxylate

Product 1

HCID 866958356-[2-(Methylthio)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-6-yl]pyridine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of methyl-6-[2-(methylthio)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-6-yl]pyridine-2-carboxylate (2.76 g, 8.72 mmol) in 1,4-dioxane (50 ml) was treated with 1.0 N NaOH(aq.) (13.09 ml, 13.09 mmol) and the reaction mixture was stirred at room temperature for 2 hours. The solvent was removed in vacuo and the residue was diluted with water. The aqueous phase was washed with diethyl ether and acidified to pH˜5-6 with 1.0 N HCl(aq.). The precipitate was collected, washed with water, ethyl acetate, and dried to give the title compound as a yellow, amorphous solid (2.52 g, 96%).

Workup

  1. customThe solvent was removed in vacuo
  2. additionthe residue was diluted with water
  3. washThe aqueous phase was washed with diethyl ether
  4. customThe precipitate was collected
  5. washwashed with water, ethyl acetate
  6. customdried

Sources & evidence

ORD record
ord-7f1bb55d3f9b4e629324a22e367e54d3
Source dataset
uspto-grants-2016_07
Patent number
US09388176B2

Reaction notes

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