Hydrochloric Acid → Mepanipyrim

HRID 2166251Notes

Reaction equation

HRID 2166251 reaction equation
[NH:1]([C:8]1[N:13]=[C:12]([CH3:14])[CH:11]=[C:10]([CH:15]=[C:16](Cl)[CH3:17])[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].Cl.C(=O)([O-])O.[Na+]>O1CCCC1.O>[NH:1]([C:8]1[N:13]=[C:12]([CH3:14])[CH:11]=[C:10]([C:15]#[C:16][CH3:17])[N:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 23665647Potassium tert-butoxideHCID 541734932-Anilino-4-methyl-6-(2-chloropropen-1-yl)pyrimidine

Product 1

HCID 86296MepanipyrimYield 93.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Into a 50 ml reaction flask equipped with a stirrer, a thermometer and a condenser, 1.30 g (0.005 mol) of 2-anilino-4-methyl-6-(2-chloropropen-1-yl)pyrimidine and 10 ml of anhydrous tetrahydrofuran were charged and dissolved, and then the mixture was cooled to -10° under stirring in a nitrogen gas atmosphere. Then, 1.28 g (0.0114 mol) of potassium tert-butoxide was dissolved in 10 ml of anhydrous tetrahydrofuran and dropwise added thereto at a temperature of from -8° to -12° C., and the mixture was stirred at -15° C. for one hour. Then, 5 ml of 1N hydrochloric acid was dropwise added thereto, and 50 ml of water and a small amount of sodium hydrogen carbonate were added to bring the pH of the aqueous layer to 7. Then, the mixture was extracted with 70 ml of toluene, and the extract was dried over anhydrous sodium sulfate. The toluene layer was concentrated and subjected to silica gel column chromatography (n-hexane/ethyl acetate=10/1) to obtain 1.04 g of 2-anilino-4-methyl-6-(1-propynyl)pyrimidine having a melting point of from 125° to 126° C. The yield was 93.2%.

Workup

  1. customInto a 50 ml reaction flask
  2. customequipped with a stirrer
  3. dissolutiondissolved
  4. temperaturethe mixture was cooled to -10°
  5. additiondropwise added
  6. stirringat a temperature of from -8° to -12° C., and the mixture was stirred at -15° C. for one hour
  7. extractionThen, the mixture was extracted with 70 ml of toluene
  8. dry with materialthe extract was dried over anhydrous sodium sulfate
  9. concentrationThe toluene layer was concentrated

Sources & evidence

ORD record
ord-3ae63d6079d04af58203cbf57d1488ec
Source dataset
uspto-grants-1990_07
Patent number
US04943675

Reaction notes

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