Ethyl 2-(benzyloxy)-3-oxopropanoate → HCID 178517543, compound

HRID 1774433

Reaction equation

HRID 1774433 reaction equation
[CH2:1]([O:8][CH:9]([CH:15]=O)[C:10]([O:12]CC)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:17][C:18]1[CH:23]=[C:22]([C:24](=[NH:26])[NH2:25])[CH:21]=[CH:20][N:19]=1>C(O)C>[CH2:1]([O:8][C:9]1[C:10]([OH:12])=[N:25][C:24]([C:22]2[CH:21]=[CH:20][N:19]=[C:18]([Cl:17])[CH:23]=2)=[N:26][CH:15]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 19903223Ethyl 2-(benzyloxy)-3-oxopropanoateHCID 509886352-Chloropyridine-4-carboximidamide

Product 1

HCID 178517543HCID 178517543, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of crude ethyl 2-(benzyloxy)-3-oxopropanoate (all from previous step), 2-chloropyridine-4-carboximidamide (9.57 g, 50 mmol) and 100 mL of anhydrous ethanol was refluxed for 4 h under nitrogen. The mixture was then cooled and the volatile solvents were removed by rotary-evaporator. The residue was re-dissolved in water and filtered. The filtrate was acidified by HCl (4N aq) in an ice bath and the white precipitate was filtered, washed with water, and dried to give 5-(benzyloxy)-2-(2-chloropyridin-4-yl)pyrimidin-4-ol (10.4 g, 66%). 1H NMR δ (400 MHz, d6-DMSO): 13.12 (s, 1H), 8.58 (d, J=5.2 Hz, 1H), 8.12 (s, 1H), 8.04 (d, J=5.2 Hz, 1H), 7.94 (s, 1H), 7.51-7.34 (m, 5H), 5.20 (s, 2H); MS (ESI) m/z (M++H)+ 314.

Workup

  1. temperaturewas refluxed for 4 h under nitrogen
  2. temperatureThe mixture was then cooled
  3. customthe volatile solvents were removed by rotary-evaporator
  4. dissolutionThe residue was re-dissolved in water
  5. filtrationfiltered
  6. customThe filtrate was acidified by HCl (4N aq) in an ice bath
  7. filtrationthe white precipitate was filtered
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-c8e27d6be1ba40568755340dbf21efba
Source dataset
uspto-grants-2016_02
Patent number
US09260413B2

Linked notes

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