Ammonia → HCID 136268156, compound

HRID 1409575Notes

Reaction equation

HRID 1409575 reaction equation
[NH3:1].CO.[Br:4][C:5]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:6]=1[CH2:7][C:8]1[N:13]=[C:12]([C:14](OC)=[O:15])[C:11]([OH:18])=[C:10]([OH:19])[N:9]=1>>[Br:4][C:5]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:6]=1[CH2:7][C:8]1[NH:9][C:10](=[O:19])[C:11]([OH:18])=[C:12]([C:14]([NH2:1])=[O:15])[N:13]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 178499084HCID 178499084, compound

Product 1

HCID 136268156HCID 136268156, compoundYield 67%

Conditions

Temperature
120 °C

Procedure

A solution of ammonia in MeOH (1 mL, 7.00 mmol) was added to a flask containing methyl 2-(2-bromo-4-fluorobenzyl)-5,6-dihydroxypyrimidine-4-carboxylate (50 mg, 140 μmol). The mixture was heated at 120° C. for 15 minutes in a microwave oven. The resulting product was collected by filtration, suspended in MeOH with Amberlyst resin and heated. The warm mixture was filtered and evaporated to dryness. The residue was triturated with Et2O and dried under vacuum to give the title compound as a white solid (0.032 g; 67%). LCMS: m/z=343 (MH+).

Workup

  1. filtrationThe resulting product was collected by filtration
  2. temperatureheated
  3. filtrationThe warm mixture was filtered
  4. customevaporated to dryness
  5. customThe residue was triturated with Et2O
  6. customdried under vacuum

Sources & evidence

ORD record
ord-c4efc9c0ad6e4fdeb2faaa36f781ff18
Source dataset
uspto-grants-2014_12
Patent number
US08921388B2

Reaction notes

Loading…