Triethylamine → HCID 59432096, compound

HRID 506473Notes

Reaction equation

HRID 506473 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:10]([CH:11]=[CH2:12])=[C:9]([NH2:13])[N:8]=[C:7]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([O:21][CH3:22])[C:15]=2[F:23])[N:6]=1)=[O:4].[Br:24]Br.C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[C:10](/[CH:11]=[CH:12]/[Br:24])=[C:9]([NH2:13])[N:8]=[C:7]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([O:21][CH3:22])[C:15]=2[F:23])[N:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24408BromineHCID 594321224-Amino-2-(4-chloro-2-fluoro-3-methoxyphenyl)-5-ethenyl-6-methoxycarbonylpyrimidine

Product 1

HCID 59432096HCID 59432096, compoundYield 56.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

6-Amino-2-(4-chloro-2-fluoro-3-methoxyphenyl)-5-vinylpyrimidine-4-carboxylic acid methyl ester (0.720 g, 2.13 mmol) was dissolved in chloroform (20 mL) and bromine (0.511 g, 3.2 mmol) was added. The reaction mixture was stirred at ambient temperature for 2 h then concentrated under vacuum. The product was dissolved in dichloromethane (20 mL), treated with triethylamine (0.430 g, 4.26 mmol), stirred at ambient temperature for 2 h, and then concentrated under vacuum. The product was purified by flash chromatography on silica gel (dichloromethane/ethyl acetate gradient) to provide the title compound (0.5 g, 56% yield over two steps) as a white solid, mp 171-173° C.: 1H NMR (CDCl3) δ 7.66 (dd, 1H), 7.22 (dd, 1H), 7.22 (d, 1H), 6.72 (d, 1H), 5.37 (br s, 2H), 4.0 (s, 3H), 3.97 (s, 3H).

Workup

  1. concentrationthen concentrated under vacuum
  2. dissolutionThe product was dissolved in dichloromethane (20 mL)
  3. stirringstirred at ambient temperature for 2 h
  4. concentrationconcentrated under vacuum
  5. customThe product was purified by flash chromatography on silica gel (dichloromethane/ethyl acetate gradient)

Sources & evidence

ORD record
ord-674e806a60aa4cbbadb0ef313b5adedc
Source dataset
uspto-grants-2010_08
Patent number
US07786044B2

Reaction notes

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