Ethyl-2,4-dioxohexanoate → HCID 66933611, compound

HRID 2069385Notes

Reaction equation

HRID 2069385 reaction equation
S(O)(O)(=O)=O.[CH3:6][S:7][C:8](=[NH:10])[NH2:9].[CH2:11]([O:13][C:14](=[O:22])[C:15](=O)[CH2:16][C:17](=O)[CH2:18][CH3:19])[CH3:12]>C(O)C>[CH2:11]([O:13][C:14]([C:15]1[CH:16]=[C:17]([CH2:18][CH3:19])[N:9]=[C:8]([S:7][CH3:6])[N:10]=1)=[O:22])[CH3:12]

Participants

4

Reactant 2

HCID 61590Ethyl-2,4-dioxohexanoateHCID 752702-Methyl-2-thiopseudourea sulfate

Product 1

HCID 66933611HCID 66933611, compoundYield 56.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of S-methylisothiourea sulphate (874 mg, 4.65 mmol) and 2,4-dioxohexanoic acid ethyl ester (800 mg, 4.65 mmol) in ethanol (4 mL) is heated to 80° C. for 48 h. The reaction mixture is then filtered, evaporated and purified by prep. TLC (using heptane/EA 1/1 as eluent) to give 590 mg of 6-ethyl-2-methylsulfanyl-pyrimidine-4-carboxylic acid ethyl ester as a yellow oil; LC-MS: tR=0.91 min, [M+H]+=227.22. 1H NMR (D6-DMSO): δ 1.24 (t, J=7.5 Hz, 3H), 1.34 (t, J=7.0 Hz, 3H), 2.56 (s, 3H), 2.81 (q, J=7.5 Hz, 2H), 4.37 (q, J=7.0 Hz, 2H), 7.58 (s, 1H).

Workup

  1. filtrationThe reaction mixture is then filtered
  2. customevaporated
  3. custompurified by prep

Sources & evidence

ORD record
ord-ee2cc047c2b8453e8be66bca36fba850
Source dataset
uspto-grants-2012_10
Patent number
US08299086B2

Reaction notes

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