Triethylamine → HCID 59432096, compound

HRID 2386146Notes

Reaction equation

HRID 2386146 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-8584c7c7ee9a48c6a7dff1c991fa7893
Source dataset
uspto-grants-2012_09
Patent number
US08268753B2

Reaction notes

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