Ethyl propiolate → 2-(4-Fluorophenoxymethyl)-2,3-dihydro-oxazolo[3,2-a]pyrimidin-7-one

HRID 237733Notes

Reaction equation

HRID 237733 reaction equation
[F:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][CH2:7][CH:8]2[O:12][C:11]([NH2:13])=[N:10][CH2:9]2)=[CH:4][CH:3]=1.[C:16](OCC)(=[O:19])[C:17]#[CH:18]>C(O)C>[F:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][CH2:7][CH:8]2[O:12][C:11]3=[N:13][C:16](=[O:19])[CH:17]=[CH:18][N:10]3[CH2:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 12182Ethyl propiolateHCID 685277115-(4-Fluoro-phenoxymethyl)-4,5-dihydro-oxazol-2-ylamine

Product 1

HCID 250723782-(4-Fluorophenoxymethyl)-2,3-dihydro-oxazolo[3,2-a]pyrimidin-7-oneYield 50%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5-(4-fluoro-phenoxymethyl)-4,5-dihydro-oxazol-2-ylamine (4.20 g, 2.00 mmol) in ethanol (8 mL) was added ethyl propiolate (0.25 g, 2.60 mmol). The reaction mixture was stirred at reflux for 6 hours. The mixture was stirred at 30° C. for a few minutes after which it was cooled to room temperature. The resulting crystals were collected and washed twice with hexane. The solid was dried under high vacuum at 65° C. for 18 hours to afford 0.23 g (50%) of 2-(4-fluorophenoxymethyl)-2,3-dihydro-oxazolo[3,2-a]pyrimidin-7-one.

Workup

  1. temperatureat reflux for 6 hours
  2. stirringThe mixture was stirred at 30° C. for a few minutes after which it
  3. customThe resulting crystals were collected
  4. washwashed twice with hexane
  5. customThe solid was dried under high vacuum at 65° C. for 18 hours

Sources & evidence

ORD record
ord-f4385d4317164461911d46d1478f1905
Source dataset
uspto-grants-2014_02
Patent number
US08642603B2

Reaction notes

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