Methyl Thioglycolate → (6-Chloro-5-formyl-2-methylsulfanyl-pyrimidin-4-ylsulfanyl)-acetic acid methyl ester

HRID 1694848Notes

Reaction equation

HRID 1694848 reaction equation
[Cl:1][C:2]1[C:7]([CH:8]=[O:9])=[C:6](Cl)[N:5]=[C:4]([S:11][CH3:12])[N:3]=1.C(N(C(C)C)C(C)C)C.[C:22]([O:26][CH3:27])(=[O:25])[CH2:23][SH:24]>C(Cl)Cl>[CH3:27][O:26][C:22](=[O:25])[CH2:23][S:24][C:6]1[C:7]([CH:8]=[O:9])=[C:2]([Cl:1])[N:3]=[C:4]([S:11][CH3:12])[N:5]=1

Participants

5

Reactant 3

HCID 16907Methyl ThioglycolateHCID 81531DiisopropylethylamineHCID 46140044,6-Dichloro-2-(methylsulfanyl)pyrimidine-5-carbaldehyde

Product 1

HCID 59376426(6-Chloro-5-formyl-2-methylsulfanyl-pyrimidin-4-ylsulfanyl)-acetic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To an ice-cooled solution (−10° C.) of 4,6-dichloro-2-methylsulfanyl-pyrimidine-5-carbaldehyde (2.0 g, 8.97 mmol) and iPr2EtN (0.82 mL, 8.97 mmol) in DCM (40 mL) was added methyl thioglycolate (1.56 mL, 8.97 mmol) in DCM (20 mL) over 15 min. The reaction mixture was let warm to RT, then washed with sat. NaHCO3, dried over MgSO4, filtered, and concentrated. The product was used without further purification. ESIMS calcd 293 (M++H), found 293 (M++H).

Workup

  1. washwashed with sat. NaHCO3
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe product was used without further purification

Sources & evidence

ORD record
ord-167f7b705a5842b0938e09f8b482385b
Source dataset
uspto-grants-2012_04
Patent number
US08158825B2

Reaction notes

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