Hydrogen Bromide → HCID 70393505, compound

HRID 4272Notes

Reaction equation

HRID 4272 reaction equation
[Cl:1][C:2]1[S:10][C:9]2[C:8](=[O:11])[N:7]([CH2:12][C:13](=[O:28])[CH2:14][C@H:15]3[C@H:20]([OH:21])[CH2:19][CH2:18][CH2:17][N:16]3C(OCC=C)=O)[CH:6]=[N:5][C:4]=2[CH:3]=1.[BrH:29]>>[BrH:29].[BrH:29].[Cl:1][C:2]1[S:10][C:9]2[C:8](=[O:11])[N:7]([CH2:12][C:13](=[O:28])[CH2:14][C@H:15]3[C@H:20]([OH:21])[CH2:19][CH2:18][CH2:17][NH:16]3)[CH:6]=[N:5][C:4]=2[CH:3]=1

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 70393848Allyl trans-2-[3-(6-chloro-3,4-dihydro-4-oxothieno[3,2-d]pyrimidin-3-yl)-2-oxopropyl]-3-hydroxy-1-piperidinecarboxylate

Product 1

HCID 70393505HCID 70393505, compound

Procedure

In a 15 ml single-neck round bottom flask equipped with a reflux condenser, a solution of 0.69 g (0.00162 mole) of allyl trans-2-[3-(6-chloro-3,4-dihydro-4-oxothieno[3,2-d]pyrimidin-3-yl)-2-oxopropyl]-3-hydroxy-1-piperidinecarboxylate and 6 ml of 48% aqueous hydrobromic acid was immersed in an oil bath preheated to 100° C. Heating was continued for 7.0 minutes. The solution was allowed to cool to room temperature, and the volatile components were evaporated under reduced pressure. Ethanol (5 ml) was added to the residue, and again the mixture was evaporated to dryness. This operation was repeated once more to afford a dark residue which was then triturated with a 1:1 solution of ethanol and acetone to furnish cream colored solid. The mixture was filtered, and the residue was dried under reduced pressure (about 1 mm Hg) to give the title compound: yield 0.50 g (61%); 1H-nmr (DMSO-d6) delta 1.3-2.0 ppm (multiplet, 4H, OCHCH2CH2CH2N), 2.8-3.0 (multiplet, 2H, COCH2CH), 3.1-3.6 (multiplet, 4H, NCH2, NCHCH2, CHOH), 5.2 (singlet, 2H, NCH2CO), 7.6 (singlet, 1H, thieno H), 8.4 (singlet, 1H, N=CH--N), 8.8 (broad singlet, 3H, NH2, NH).

Workup

  1. customIn a 15 ml single-neck round bottom flask equipped with a reflux condenser
  2. custompreheated to 100° C
  3. temperatureHeating
  4. customthe volatile components were evaporated under reduced pressure
  5. additionEthanol (5 ml) was added to the residue
  6. customagain the mixture was evaporated to dryness
  7. customto afford a dark residue which
  8. customwas then triturated with a 1:1 solution of ethanol and acetone
  9. customto furnish cream colored solid
  10. filtrationThe mixture was filtered
  11. customthe residue was dried under reduced pressure (about 1 mm Hg)

Sources & evidence

ORD record
ord-0a4cb4e545e64cc5b3c6911886f99a0d
Source dataset
uspto-grants-1988_02
Patent number
US04725599

Reaction notes

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