Ammonia → HCID 118598838, compound

HRID 1050405Notes

Reaction equation

HRID 1050405 reaction equation
[Br:1][C:2]1[C:7](=[O:8])[NH:6][C:5]([C:9]([O:11]CC)=O)=[N:4][CH:3]=1.[NH3:14]>C(O)C>[Br:1][C:2]1[C:7](=[O:8])[NH:6][C:5]([C:9]([NH2:14])=[O:11])=[N:4][CH:3]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 118598640HCID 118598640, compound

Product 1

HCID 118598838HCID 118598838, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of ethyl 5-bromo-6-oxo-1,6-dihydropyrimidine-2-carboxylate (4, 0.2 g, 0.81 mmol) in ethanol (4 mL), liquid ammonia (4 mL) was added dropwise at room temperature. The reaction mixture was heated at 50° C. for 16 h. TLC showed consumption of starting material. Solvent was removed under reduced pressure and the residue was treated with methanol (1 mL) and filtered. The solid was washed with diethyl ether and dried under reduced pressure to afford 5-bromo-6-oxo-1,6-dihydropyrimidine-2-carboxamide (5) as off white solid. Yield: 0.14 g, 76%; MS (ESI) m/z 218.87 [M+1]+.

Workup

  1. customconsumption of starting material
  2. customSolvent was removed under reduced pressure
  3. additionthe residue was treated with methanol (1 mL)
  4. filtrationfiltered
  5. washThe solid was washed with diethyl ether
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-efe57679f7cd47aa8b8f4307b7a3b171
Source dataset
uspto-grants-2016_07
Patent number
US09382248B2

Reaction notes

Loading…