Hydrogen Bromide → trans-3-[3-(3-Hydroxy-2-piperidyl)-2-oxopropyl]benzofuro[3,2-d]pyrimidin-4(3H)-one Dihydrobromide

HRID 4275Notes

Reaction equation

HRID 4275 reaction equation
[O:1]=[C:2]1[N:7]([CH2:8][C:9](=[O:23])[CH2:10][C@H:11]2[C@H:16]([O:17]C)[CH2:15][CH2:14][CH2:13][N:12]2C(OC)=O)[CH:6]=[N:5][C:4]2[C:24]3[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=3[O:26][C:3]1=2.[BrH:31]>C(O)C>[BrH:31].[BrH:31].[OH:17][C@@H:16]1[CH2:15][CH2:14][CH2:13][NH:12][C@H:11]1[CH2:10][C:9](=[O:23])[CH2:8][N:7]1[C:2](=[O:1])[C:3]2[O:26][C:25]3[CH:27]=[CH:28][CH:29]=[CH:30][C:24]=3[C:4]=2[N:5]=[CH:6]1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 70393670Methyl trans-2-[3-(3,4-dihydro-4-oxobenzofuro[3,2-d]pyrimidin-3-yl)-2-oxopropyl]-3-methoxy-1-piperidinecarboxylate

Product 1

HCID 70394007trans-3-[3-(3-Hydroxy-2-piperidyl)-2-oxopropyl]benzofuro[3,2-d]pyrimidin-4(3H)-one Dihydrobromide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 0.600 g (0.00145 mole) of methyl trans-2-[3-(3,4-dihydro-4-oxobenzofuro[3,2-d]pyrimidin-3-yl)-2-oxopropyl]-3-methoxy-1-piperidinecarboxylate and 30 ml of 48% hydrobromic acid in a 100 ml round bottom flask was immersed in a bath preheated to 150° C. and held there for 12 minutes. Upon cooling to room temperature, the solution was evaporated under reduced pressure to afford a residue. The residue was heated with ethanol briefly; the mixture was allowed to cool, and the ethanol removed by pipette to furnish the title compound: m.p. 257°-258° C.; yield 0.28 g (41%); 1H-nmr (DMSO-d6) delta 1.4-2.0 ppm (multiplet, 4H, CH3OCHCH2CH2CH2N), 2.8-3.0 (multiplet, 2H, NCH2), 3.1-3.5 (multiplet, includes H2O, CHOH, COCH2CH, and CH2CHNCO), 5.2 (singlet, 2H, NCH2CO), 7.5 (triplet, 1H, aromatic H), 7.7 (triplet, 1H, aromatic H), 7.9 (doublet, 1H, aromatic H), 8.1 (doublet, 1H, aromatic H), 8.4 (singlet, 1H, N=CH--N), 8.7 (broad singlet, 1H, OH).

Workup

  1. custompreheated to 150° C.
  2. customthe solution was evaporated under reduced pressure
  3. customto afford a residue
  4. temperatureto cool
  5. customthe ethanol removed by pipette

Sources & evidence

ORD record
ord-e73b22e82350428eb477a670f319f5f9
Source dataset
uspto-grants-1988_02
Patent number
US04725599

Reaction notes

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