Bromine → HCID 57606978, compound

HRID 886798Notes

Reaction equation

HRID 886798 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([CH3:16])[C:5]2[CH:11]=[CH:10][C:9](=[O:12])[N:8]([CH:13]([CH3:15])[CH3:14])[C:6]=2[N:7]=1.[Br:17]Br>C(Cl)Cl>[NH2:1][C:2]1[N:3]=[C:4]([CH3:16])[C:5]2[CH:11]=[C:10]([Br:17])[C:9](=[O:12])[N:8]([CH:13]([CH3:14])[CH3:15])[C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 57606975HCID 57606975, compound

Product 1

HCID 57606978HCID 57606978, compoundYield 56.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-amino-8-isopropyl-4-methylpyrido[2,3-d]pyrimidin-7(8H)-one (2.88 g, 13.19 mmol) dissolved in 80 mL of DCM at 0° C., (4.21 g, 26.39 mmol) bromine was added. Reaction vessel was removed from ice bath and allowed to react at room temperature over night. LCMS indicated complete conversion of starting material to product. Sample was evaporated to remove DCM and excess bromine. Orange solid was diluted in ethyl acetate and extracted with 10% NaHSO3, H2O, and brine. Organic layer was dried over Na2SO4, filtered, and reduced to dryness yielding 2-amino-6-bromo-8-isopropyl-4-methylpyrido[2,3-d]pyrimidin-7(8H)-one as a light yellow powder (2.2 g, 56% yield). 1H NMR (400 MHz, CDCl3) δ 8.08 (s, 1H), 5.83 (m, 1H), 5.69 (br s, 2H), 2.60 (s, 3H), 1.58 (d, J=6.8, 6H).

Workup

  1. customReaction vessel
  2. customwas removed from ice bath
  3. customto react at room temperature over night
  4. customSample was evaporated
  5. customto remove DCM and excess bromine
  6. additionOrange solid was diluted in ethyl acetate
  7. extractionextracted with 10% NaHSO3, H2O, and brine
  8. dry with materialOrganic layer was dried over Na2SO4
  9. filtrationfiltered

Sources & evidence

ORD record
ord-77f916286edf4edfb54ee24a9ceb38b2
Source dataset
uspto-grants-2012_08
Patent number
US08247408B2

Reaction notes

Loading…