Ethyl propiolate → (S)-2-(4-tert-butyl-phenoxymethyl)-2,3-dihydro-oxazolo[3,2-a]pyrimidin-7-one

HRID 237731Notes

Reaction equation

HRID 237731 reaction equation
[C:1]([C:5]1[CH:18]=[CH:17][C:8]([O:9][CH2:10][C@H:11]2[O:15][C:14]([NH2:16])=[N:13][CH2:12]2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:19](OCC)(=[O:22])[C:20]#[CH:21]>C(O)C>[C:1]([C:5]1[CH:18]=[CH:17][C:8]([O:9][CH2:10][C@H:11]2[O:15][C:14]3=[N:16][C:19](=[O:22])[CH:20]=[CH:21][N:13]3[CH2:12]2)=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 12182Ethyl propiolateHCID 67060987(S)-5-(4-tert-butyl-phenoxymethyl)-4,5-dihydro-oxazol-2-ylamine

Product 1

HCID 25073615(S)-2-(4-tert-butyl-phenoxymethyl)-2,3-dihydro-oxazolo[3,2-a]pyrimidin-7-oneYield 50.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (S)-5-(4-tert-butyl-phenoxymethyl)-4,5-dihydro-oxazol-2-ylamine (4.53 g, 18.3 mmol) in ethanol (35 mL) was added ethyl propiolate (2.32 g, 23.7 mmol). The reaction mixture was stirred at reflux for 6 hours. The mixture was stirred at 30° C. for a few minutes and subsequently 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 2.8 g (50%) of (S)-2-(4-tert-butyl-phenoxymethyl)-2,3-dihydro-oxazolo[3,2-a]pyrimidin-7-one. [α]D25 −54.04 (c 0.503, CHCl3).

Workup

  1. temperatureat reflux for 6 hours
  2. stirringThe mixture was stirred at 30° C. for a few minutes
  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-33cc2b5453344cb3a9479041f9b6ec5f
Source dataset
uspto-grants-2014_02
Patent number
US08642603B2

Reaction notes

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