Acetic Acid → HCID 16124582, compound

HRID 1666280Notes

Reaction equation

HRID 1666280 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 (E) 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-599acae89b8045f698306c2fd9ca7f85
Source dataset
uspto-grants-2011_10
Patent number
US08044062B2

Reaction notes

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