Sodium Hydroxide → 1-[(3,4-Dimethoxy-benzyl)-6,7-dimethoxy-1,2,3,4-tetrahydro-naphthalen-2-yl]-pyrimidin-acetic acid

HRID 48573Notes

Reaction equation

HRID 48573 reaction equation
C([O:3][C:4](=[O:37])[CH2:5][CH:6]1[N:11]=[CH:10][CH:9]=[CH:8][N:7]1[CH:12]1[CH2:21][CH2:20][C:19]2[C:14](=[CH:15][C:16]([O:24][CH3:25])=[C:17]([O:22][CH3:23])[CH:18]=2)[CH:13]1[CH2:26][C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[C:29]([O:35][CH3:36])[CH:28]=1)C.[OH-].[Na+]>O1CCOCC1.CO>[CH3:36][O:35][C:29]1[CH:28]=[C:27]([CH:32]=[CH:31][C:30]=1[O:33][CH3:34])[CH2:26][CH:13]1[C:14]2[C:19](=[CH:18][C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=2)[CH2:20][CH2:21][CH:12]1[N:7]1[CH:8]=[CH:9][CH:10]=[N:11][CH:6]1[CH2:5][C:4]([OH:37])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 698959611-[(3,4-Dimethoxy-benzyl)-6,7-dimethoxy-1,2,3,4-tetrahydro-naphthalen-2-yl]-pyrimidin-acetic acid ethyl ester

Product 1

HCID 698962331-[(3,4-Dimethoxy-benzyl)-6,7-dimethoxy-1,2,3,4-tetrahydro-naphthalen-2-yl]-pyrimidin-acetic acidYield 93.1%

Reagents, catalysts & solvents 1

HCID 21966525Dioxane MethanolSolvent

Procedure

To a solution of 1-[(3,4-Dimethoxy-benzyl)-6,7-dimethoxy-1,2,3,4-tetrahydro-naphthalen-2-yl]-pyrimidin-acetic acid ethyl ester (1.4 g, 2.75 mmol) in a mixture dioxane/MeOH (4/3) (35 ml) was added dropwise 2M NaOH(aq) (24 ml). The resulting mixture was stirred at RT for 20 h under nitrogen. The mixture was then concentrated in vacuo, combined with water and AcOEt. The aqueous phase was acidified until pH 1 with 2N HCl, extracted three times with with CH2Cl2, the combined organic phases were dried over anhydrous MgSO4, filtered and concentrated to give the titled product (1.23 g, 93%) as yellow-green crystals.

Workup

  1. concentrationThe mixture was then concentrated in vacuo
  2. extractionextracted three times with with CH2Cl2
  3. dry with materialthe combined organic phases were dried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0299b778713f490fb002e9de92912d20
Source dataset
uspto-grants-2004_03
Patent number
US06703392B2

Reaction notes

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