Thiophosgene → HCID 86632891, compound

HRID 1628515Notes

Reaction equation

HRID 1628515 reaction equation
[C:1](Cl)(Cl)=[S:2].[CH2:5]([C:7]1[C:12]([NH2:13])=[C:11]([CH2:14][CH3:15])[N:10]=[C:9]([CH3:16])[N:8]=1)[CH3:6]>O1CCCC1.C(=O)([O-])O.[Na+]>[CH2:14]([C:11]1[C:12]([N:13]=[C:1]=[S:2])=[C:7]([CH2:5][CH3:6])[N:8]=[C:9]([CH3:16])[N:10]=1)[CH3:15]

Participants

5

Reactant 2

HCID 10040ThiophosgeneHCID 68736697HCID 68736697, compound

Product 1

HCID 86632891HCID 86632891, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent2×

Conditions

Temperature
0 °C

Procedure

Thiophosgene (2.53 mL, 33.2 mmol) was added dropwise to a stirred mixture of 4,6-diethyl-2-methylpyrimidin-5-amine (4.22 g, 25.5 mmol) in tetrahydrofuran (40 mL) and saturated aqueous sodium hydrogen carbonate (40 mL) at 0° C., and the mixture was stirred at 0° C. for 20 minutes. The mixture was diluted with saturated aqueous sodium hydrogen carbonate, and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to give the title compound as a pale yellow solid (5.28 g, 25.5 mmol, 100%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4422489750bf46a09561a381e919e422
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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