Sodium Methoxide → HCID 178450819, compound

HRID 2169215Notes

Reaction equation

HRID 2169215 reaction equation
Cl.[Cl:2][C:3]1[C:8]([Cl:9])=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:10][C:11]([NH2:13])=[NH:12].C[O:15][C:16](=O)/[C:17](/[O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[C:18](\O)/[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20].C[O-].[Na+]>CO>[C:22]([O:21][C:19]([C:18]1[C:17]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[C:16]([OH:15])[N:13]=[C:11]([CH2:10][C:4]2[CH:5]=[CH:6][CH:7]=[C:8]([Cl:9])[C:3]=2[Cl:2])[N:12]=1)=[O:20])([CH3:25])([CH3:23])[CH3:24]

Participants

5

Reactant 3

HCID 10942334Sodium MethoxideHCID 546790054-Tert-butyl 1-methyl 2-(benzyloxy)-3-hydroxyfumarateHCID 867258632-(2,3-Dichlorophenyl)-acetamidine hydrochloride

Product 1

HCID 178450819HCID 178450819, compoundYield 57.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 2-(2,3-dichlorophenyl)-acetamidine hydrochloride salt (129) (10 g, 41.84 mmol) and (E)-2-benzyloxy-3-hydroxy-but-2-enedioic acid 4-tert-butyl ester 1-methyl ester (4) (19.33 g, 62.76 mmol) in methanol (300 mL) was added sodium methoxide (6.7 g, 125.52 mmol) at 0° C. Then the reaction mixture was allowed to warm to room temperature, and was stirred for 16 h. After completion of the reaction, it was quenched with 1N HCl, the methanol was evaporated and water was added. The mixture was extracted with ethyl acetate and the separated organic part was dried over sodium sulfate and concentrated under reduced pressure to get a crude product, which was purified by a normal silica column using 30% ethyl acetate in hexane to get 5-benzyloxy-2-(2,3-dichlorobenzyl)-6-hydroxypyrimidine-4-carboxylic acid tert-butyl ester (130) (10 g, 57.8%) as a brown solid.

Workup

  1. customAfter completion of the reaction, it
  2. customwas quenched with 1N HCl
  3. customthe methanol was evaporated
  4. additionwater was added
  5. extractionThe mixture was extracted with ethyl acetate
  6. dry with materialthe separated organic part was dried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customto get a crude product, which
  9. customwas purified by a normal silica column

Sources & evidence

ORD record
ord-cb060c5922ad4d518b82e922614ce453
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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