Hydrochloric Acid → HCID 86604627, compound

HRID 1678053Notes

Reaction equation

HRID 1678053 reaction equation
CO[C:3]([C:5]1[C:6](Cl)=[N:7][CH:8]=[N:9][C:10]=1[Cl:11])=[O:4].[SH:13][CH2:14][C:15]([O:17][CH2:18]C)=[O:16].C(N(CC)CC)C.Cl>C(#N)C.O>[CH3:18][O:17][C:15]([C:14]1[S:13][C:6]2[N:7]=[CH:8][N:9]=[C:10]([Cl:11])[C:5]=2[C:3]=1[OH:4])=[O:16]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 12185Ethyl ThioglycolateHCID 24820741Methyl 4,6-dichloropyrimidine-5-carboxylate

Product 1

HCID 86604627HCID 86604627, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4,6-Dichloropyrimidine-5-carboxylic acid methyl ester (0.5 g, 2.5 mmol) (prepared as disclosed in Lee, C.-H., et. al. Bioorganic & Medicinal Chemistry Letters (2001), 11(18), 2419) and mercaptoacetic acid, ethyl ester (0.29 g 2.5 mmol) in acetonitrile (50 mL) was added triethylamine (2 mL) and the solution warmed to 50° C. for one hour. The reaction mixture was diluted with water (100 mL), made acidic (pH 2) with 2N HCl and the precipitate collected by filtration, giving product as a white solid, (0.6 g, 2.3 mmol, 92 percent) yield.

Workup

  1. filtrationthe precipitate collected by filtration

Sources & evidence

ORD record
ord-b8e5a5838cf54bd4be052724dfd02f47
Source dataset
uspto-grants-2011_08
Patent number
US08008487B2

Reaction notes

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