Acetic Acid → HCID 16124582, compound

HRID 1893917Notes

Reaction equation

HRID 1893917 reaction equation
[CH2:1]([NH:3][C:4]1[N:5]=[C:6]([CH3:20])[C:7]2[CH:13]=[CH:12][C:11](=[O:14])[N:10]([CH2:15][CH2:16][CH2:17][O:18][CH3:19])[C:8]=2[N:9]=1)[CH3:2].C(O)(=O)C.[Br:25]Br>C(Cl)Cl.O>[Br:25][C:12]1[C:11](=[O:14])[N:10]([CH2:15][CH2:16][CH2:17][O:18][CH3:19])[C:8]2[N:9]=[C:4]([NH:3][CH2:1][CH3:2])[N:5]=[C:6]([CH3:20])[C:7]=2[CH:13]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 24408BromineHCID 57930765HCID 57930765, compound

Product 1

HCID 16124582HCID 16124582, compoundYield 56.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-(ethylamino)-8-(3-methoxypropyl)-4-methylpyrido[2,3-d]pyrimidin-7(8H)-one (0.18 g, 0.65 mmol), acetic acid (5 mL) and dichloromethane (3 mL) was added bromine (36 ul, 0.7 mmol). The mixture was stirred for 5 minutes, and then diluted with DCM and water. The organic layer was washed with sat. sodium bicarbonate (3 times), brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by flash column chromatography to gave 0.13 g (56% yield) of 6-bromo-2-(ethylamino)-8-(3-methoxypropyl)-4-methylpyrido[2,3-d]pyrimidin-7(8H)-one. 1H NMR (400 MHz, CDCl3) δ 8.09 (s, 1H), 5.44 (Br. s, 1H), 4.55 (m, 2H), 3.54-3.47 (m, 4H), 3.33 (s, 3H), 2.53 (s, 3H), 2.05-2.00 (m, 2H), 1.30-1.23 (m, 3H); MS (EI) for C14H19BrN4O2: 355 (MH+).

Workup

  1. washThe organic layer was washed with sat. sodium bicarbonate (3 times), brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by flash column chromatography

Sources & evidence

ORD record
ord-ff62d78f4ba64844ad96327159086395
Source dataset
uspto-grants-2013_08
Patent number
US08513266B2

Reaction notes

Loading…